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Quality Control of [ 492-30-8 ] Purity: 97% SDS Specification

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Product Details of [ 492-30-8 ]

CAS No. :	492-30-8
Formula :	C₆H₁₀O₅
M.W :	162.14
SMILES Code :	O=C1O[C@H](CO)[C@@H](O)[C@]1(O)C
MDL No. :	MFCD07369541
InChI Key :	WJBVKNHJSHYNHO-ZMIZWQJLSA-N
Pubchem ID :	11805069

Safety of [ 492-30-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 492-30-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	0
Fraction Csp3	0.83
Num. rotatable bonds	1
Num. H-bond acceptors	5.0
Num. H-bond donors	3.0
Molar Refractivity	33.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	86.99 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.31
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-1.22
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-1.98
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-1.05

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.01
Solubility	158.0 mg/ml ; 0.976 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.11
Solubility	125.0 mg/ml ; 0.773 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.8
Solubility	1020.0 mg/ml ; 6.27 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-8.16 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.04

Application In Synthesis of [ 492-30-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 492-30-8 ]

[ 492-30-8 ] Synthesis Path-Downstream 1~32

1
[ 492-30-8 ]
[ 582310-87-0 ]

References: [1]Acta Chemica Scandinavica (1947),1965,vol. 19,p. 1127 - 1134.

2
[ 492-30-8 ]
[ 23669-84-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1969,vol. 34,p. 857 - 866.

3
[ 492-30-8 ]
[ 614-31-3 ]
[ 23669-85-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1969,vol. 34,p. 857 - 866.

4
[ 492-30-8 ]
[ 67-64-1 ]
[ 23709-41-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid; at 20℃; for 16h;Cooling with ice; Inert atmosphere;	2-C-Methyl-D-ribono-1,4-lactone (50 g, 0.31 mol) was dissolved in acetone (1 L) and the solution was cooled using an ice bath followed by slow dropwise addition of conc. H2SO4(20 mL). The reaction mixture was stirred at room temperature under nitrogen for 16 h. Solid Na2CO3was added slowly to a pH of 6. The resultant mixture was filtered to remove inorganic salts and filtrate was evaporated. The oily residue was redissolved in dichloromethane and further purified by passing through a silica plug to yield 55 g of product (3.1) as off-white solids (89percent yield).
86%	With sulfuric acid; at 20℃;	Concentrated sulphuric acid (12 mL) was added to a suspension of <strong>[492-30-8](3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one</strong> (100g, 616 mmol) in acetone (1200 mL). The mixture was stirred at room temperature overnight. The pH was then adjusted to pH 8.0 with concentrated ammonia and the mixture was filtered and concentrated in vacuo. The residue obtained was partitioned between ether and water. The organic layer was successively washed brine, dried (MgSO4), and concentrated in vacuo to give 107 g (86percent) of the alcohol as a yellow oil that solidified overnight. Rf 0.42 (1:1 iso-hexane:EtOAc); 1H NMR (CDCl3) delta 1.40 (s, 3H), 1.42 (s, 3H), 1.64 (s, 3H), 2.87 (br s, 1H, OH), 3.80 (m, 2H), 3.97 (m, 2H), 4.53 (m, 2H).
	With sulfuric acid; at 20℃; for 3h;	To a stirred suspension of 285-1 (300 g, 1.86 mol) in acetone (4 L) was added conc.H2SO4 (56 mL) dropwiseat RT. The mixture was stirred at RT for 3 h. The mixture was neutralized with solid NaHCO3 and filtered.The filtrate was evaporated under reduced pressure to give 285-2 (381 g, crude) as a colorless oil, which wasused for the next step without further purification

With sulfuric acid; at 20℃; for 3h;

To a stirred suspension of 278-1(300 g, 1.86 mol) in acetone (4 pL) was added conc. H2S04 (56 mE) dropwise at RT. The mixture was stirred at R.T. for 3 h. The mixture was neutralized with solid NaHCO3 and filtered. The filtrate was evaporated under reduced pressure to give 278-2 (381 g, crude) as a colorless oil, which was used for the next step without further purification.

References: [1]Tetrahedron Letters,2007,vol. 48,p. 517 - 520.
[2]Tetrahedron Asymmetry,2007,vol. 18,p. 500 - 512.
[3]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 577 - 580.
[4]Synlett,2007,p. 3149 - 3154.
[5]Tetrahedron Letters,2009,vol. 50,p. 5088 - 5093.
[6]Journal of the American Chemical Society,1983,vol. 105,p. 1988 - 2006.
[7]Patent: KR101525420,2015,B1 .Location in patent: Paragraph 0091-0093.
[8]Tetrahedron Letters,2011,vol. 52,p. 6415 - 6419.
[9]Journal of the American Chemical Society,1980,vol. 102,p. 1155 - 1157.
[10]Journal of the American Chemical Society,1985,vol. 107,p. 3285 - 3294.
[11]Tetrahedron Asymmetry,2008,vol. 19,p. 2417 - 2424.
[12]Tetrahedron,2010,vol. 66,p. 4307 - 4317.
[13]Patent: US2015/105341,2015,A1 .Location in patent: Paragraph 1208.
[14]Patent: US2015/366888,2015,A1 .Location in patent: Paragraph 1135; 1136.

5
[ 157666-05-2 ]
[ 492-30-8 ]

References: [1]Journal of Carbohydrate Chemistry,1994,vol. 13,p. 767 - 776.

6
[ 492-30-8 ]
[ 18162-48-6 ]
(3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-3-methyl-dihydro-furan-2-one [ No CAS ]

References: [1]Tetrahedron Letters,1995,vol. 36,p. 2141 - 2144.

7
N,N-dimethyl-1-amino-1-deoxy-D-fructose [ No CAS ]
[ 492-30-8 ]

Yield	Reaction Conditions	Operation in experiment
		D-Glucose (90.1 g) was suspended in absolute ethanol (130 mL) with acetic acid (30.0 g) and was charged to a reactor at 20 0C. Dimethylamine solution (33percent solution in absolute ethanol, 69.7 g) was added to the suspension within 30 minutes at 20 0C (exothermic), and a dropping funnel employed for additions to the reactor was rinsed with absolute ethanol (5 mL). The reaction mixture was heated to 75 0C. within a 30 minute period, then cooled to 55 0C. within 1 hour, and maintained at 55 0C. for an additional 2 hours, to afford a orange solution. The orange solution then was concentrated at 50 0C. in vacuo to provide a brown oil. Water (190 g) was then added to the brown oil, and the reactor was evacuated three times to approximately 100 mbar and each time was relieved with nitrogen, following which a weak nitrogen flow was continued. Calcium oxide (36.5 g) was added in 4 portions at 10 minute intervals at15 0C, with rises of approximately 5 0C. in internal temperature observed after addition of each portion. The reactor was evacuated twice to approximately 100 mbar and relieved with nitrogen, following which a weak nitrogen flow was continued. The mixture then was heated to an internal temperature of 25 0C within about 20 minutes, then heated to an internal temperature of 40 0C. within 18 hours, following which it was stirred at an internal temperature of 40 0C for four hours, and finally cooled to an internal temperature of 3 0C. 96percent sulfuric acid (80.6 g) was added over a 2 hour period while maintaining an internal temperature of 3 0C to provide a yellow colored mixture. The pH was checked to reach a targeted pH of between 2.4 and 2.7; EPO <DP n="29"/>if the pH was >2.7, sulfuric acid was added to reach the target value. The yellow mixture next was heated to an internal temperature of 45 0C within 30 minutes, stirred for 12 hours while maintaining the 45 0C internal temperature, and then cooled to 25 0C. Calcium sulfate that formed was removed by filtration through a scintered glass funnel into a 2 L. filter flask, and the filtration residue was washed via the reactor in three portions of water (100 g per portion) to provide a brown filtrate. This filtrate was concentrated at a temperature of 50 0C and pressure of 40 mbar by use of a rotary film evaporator, and then was degassed at 50 0C and 20 ~^ 10 mbar for 1 hour. Next, acetone (500 mL), water (50 g) and Fuller's earth (50 g) were added to the concentrated filtrate, and this mixture was refluxed for 30 minutes, after which the upper liquid phase was decanted and filtered through a cellflock pad. The lower phase was extracted twice with acetone (250 mL) and water (25 g) under reflux for 5 minutes. The upper liquid phase was decanted and filtered through a cellflock pad for each of the two extractions. Next, the combined filtrates were concentrated at a temperature of 50 0C and 450 mbar by using a rotary film evaporator, and the degassed at 50 0C and 20 -^ 10 mbar for 1 hour to provide 60.8 g of crude product as a dark brown solid. Acetone (90 mL) was added to the crude product at a temperature of 60 0C. over a 10 minute time period, and the mixture was stirred at 60 0C, then at an internal temperature of 50-56 0C for 5-15 minutes to afford a suspension in a volume of 200 mL. Next, the mixture containing the suspension was cooled to an internal temperature of 20 0C, and the contents were stirred for 2 hours while maintaining the internal temperature at 20 0C. The mixture then was filtered through a scintered glass funnel (porosity 3), and the filter cake washed twice with acetone (15 mL) at room temperature to provide the final product. The final product was dried in vacuum at 50 0C for 5 hours to afford 28.7 g of 2-C-Methyl-D-ribono-l,4-lactone as a yellow-white solid. EPO <DP n="30"/>
		D-Glucose (3.17 g, 17.6 mmol) was suspended in ethanol (5 niL) with glacial acetic acid (1 niL). Dimethylamine solution (33percent solution in methylated spirits, 3.2 mL, 18.0 mmol) was added to the suspension and the reaction mixture stirred at 80 0C for one and a half hours. The resulting dark orange solution was concentrated in vacuo to afford a crude dark orange-brown oil (6.55 g). The crude product mixture was then dissolved in water (150 mL) and stirred at 70 0C with calcium oxide (5.6fg, 100 mmol) for 24 hours when TLC analysis (chloroform:methanol:water:acetic acid, 60:30:5:3) revealed no starting materials (Rf 0.09 0.24) and only baseline products. LRMS analysis (ESI -ve) of the crude alkaline reaction mixture showed only one major peak at 179.01 Da. Oxalic acid dihydrate (6.74 g, 53.5 mmol) was added to the suspension to afford a pale pink precipitate suspended in a solution with a measured pH of 10. The mixture was allowed to cool to room temperature, filtered through a pad of Celite.(R). with water and the filtrate passed through Amberlite.(R). IR 120 ion exchange resin, using water as eluent. The water was then removed under reduced pressure to afford a crude orange oil (2.39 g). The crude product was dissolved in water (50 mL) and heated at 40 0C for 15 minutes. TLC analysis (15percent methanol in dichloromethane) revealed the presence of one major product (Rf 0.38) and LRMS analysis (ESI -ve) revealed no peak at 179.01 Da and a major peak at 161.15 Da. The water was removed under reduced pressure and the crude product purified by flash column chromatography (ethyl acetate: cyclohexane, (1:1) --> ethyl acetate) and subsequently by recrystallisation from ethyl acetate by the addition of cyclohexane to afford 2-C-methyl-D-ribono-l,4-lactone (534 mg, 19percent) as a white crystalline solid; mp 158-159 0C {Lit. 160-161 0C); [alpha]^5 +87.5 (c 0.76 in water) {Lit. [alpha.pound.° +93 (water)}; vmax(film): 3356 (br, O-H), 1773 (gamma-lactone C=O) cm4; deltaH (CD3OD, 400 EPO <DP n="31"/>MHz): 1.40 (3H, CH3), 3.71 (IH, dd, J4)5 4.5 Hz, J5,5> 12.8Hz, H-5), 3.90 (IH, d, J3j4 7.8 Hz, H-3), 3.94 (IH, dd, J4,5> 2.4 Hz, J5)5' 12.8 Hz, H-5'), 4.29 (IH, ddd, J4,s 4.5 Hz, J4)5> 2.4 Hz, J3)4 7.8 Hz, H-4); deltac (CD3OD, 100.6 MHz): 20.02 (CH3), 60.03 (C-5), 72.55 (C-2), 72.64 (C-3), 83.43 (C-4), 176.97 (C-I); LRMS m/z (ESI -ve): 161.04 (M-H+, 100percent), 183.00 (M+Na+-2H+, 47percent); HRMS m/z (ESI -ve): found 161.0455 (M-H+); C6H9O5 requires 161.0450.

References: [1]Tetrahedron Letters,2006,vol. 47,p. 315 - 318.
[2]Patent: WO2007/25304,2007,A2 .Location in patent: Page/Page column 27-28; 1/6; 2/6.
[3]Patent: WO2007/25304,2007,A2 .Location in patent: Page/Page column 29-30; 1/6.

8
[ 54917-60-1 ]
[ 492-30-8 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 315 - 318.

9
[ 143-33-9 ]
[ 138811-35-5 ]
[ 850359-46-5 ]
[ 492-30-8 ]
[ 53008-90-5 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 315 - 318.
[2]Tetrahedron Letters,2007,vol. 48,p. 4441 - 4444.

10
[ 492-30-8 ]
4-amino-1-[(2R,3R, 4S, 5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methylthiolan-2-yl]-1,2-dihydropyrimidine-2-one [ No CAS ]