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Quality Control of H-Thr(Me)-OH Purity: 98% SDS Specification

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Product Details of H-Thr(Me)-OH

CAS No. :	4144-02-9
Formula :	C₅H₁₁NO₃
M.W :	133.15
SMILES Code :	N[C@@H]([C@H](OC)C)C(O)=O
MDL No. :	MFCD00037767
InChI Key :	FYCWLJLGIAUCCL-DMTCNVIQSA-N
Pubchem ID :	2724875

Safety of H-Thr(Me)-OH

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

Application In Synthesis of H-Thr(Me)-OH

* 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.

Upstream synthesis route of [ 4144-02-9 ]
Downstream synthetic route of [ 4144-02-9 ]

[ 4144-02-9 ] Synthesis Path-Upstream 1~5

1
[ 4144-14-3 ]
[ 4144-02-9 ]

References: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1447 - 1449.

2
[ 70561-63-6 ]
[ 4144-02-9 ]

References: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1447 - 1449.

3
[ 44975-87-3 ]
[ 4144-02-9 ]

References: [1] Journal of Biological Chemistry, 1937, vol. 119, p. 104,105[2] Org.Synth.Coll.Vol., 1955, vol. III, p. 813.

4
[ 2076-53-1 ]
[ 4144-02-9 ]

References: [1] Journal of Biological Chemistry, 1937, vol. 119, p. 104,105[2] Org.Synth.Coll.Vol., 1955, vol. III, p. 813.

5
[ 6622-23-7 ]
[ 4144-02-9 ]

References: [1] Journal of Biological Chemistry, 1937, vol. 119, p. 104,105[2] Org.Synth.Coll.Vol., 1955, vol. III, p. 813.

[ 4144-02-9 ] Synthesis Path-Downstream 1~32

1
[ 4144-02-9 ]
[ 72-19-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sulfuric acid; sodium nitrite; In water; at 0 - 5℃;	To a solution of <strong>[4144-02-9](2S,3R)-2-amino-3-methoxybutanoic acid</strong> (CAS Number: 4144-02-9; Ark Pharm, lnc.)(lg, 7.5 mmol) in 1M sulfuric acid (15 ml, 1M aqueous solution), cooled to 0C, was added a solution of sodium nitrite (1.0 g, 15 mmol) in water (8 ml). The temperature was maintained below 5C during the addition, and the mixture was stirred at such overnight. Thesolution was then saturated with ammonium sulfate, extracted with diethyl ether (5x25 ml), driedover sodium sulfate and evaporated under reduced pressure giving 60a (0.27 g, 67%) as acolorless oil that crystallized on standing. 1H NMR (400 MHz, CDCI3): 54.14 (d, J= 3.6 Hz, 1H),3.81 (qd, J= 6.4, 3.6 Hz, 1H), 3.41 (s, 3H), 1.25 (d, J= 6.4 Hz, 3H). LCMS (mlz) 132.9 [M-H], Tr= 0.39 mm.

References: [1]Patent: WO2013/185093,2013,A1 .Location in patent: Page/Page column 233.
[2]Nippon Kagaku Zasshi,1950,vol. 71,p. 500.
Chem.Abstr.,1951,p. 9483.

2
[ 4144-02-9 ]
[ 26839-91-8 ]

References: [1]Nippon Kagaku Zasshi,1950,vol. 71,p. 500.
Chem.Abstr.,1951,p. 9483.

3
[ 44975-87-3 ]
[ 4144-02-9 ]

References: [1]Journal of Biological Chemistry,1937,vol. 119,p. 104,105.
Org.Synth.Coll.Vol.,1955,vol. III,p. 813.

4
(2S,3R)-2-Benzyloxycarbonylamino-3-methoxy-butyric acid; compound with dicyclohexyl-amine [ No CAS ]
[ 4144-02-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,1965,vol. 30,p. 2592 - 2599.

5
[ 4144-14-3 ]
[ 4144-02-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1447 - 1449.

6
[ 4144-02-9 ]
(E)-(S)-4-[((2S,3R)-2-tert-Butoxycarbonylamino-3-methoxy-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.

7
[ 4144-02-9 ]
(E)-(S)-4-[(2S,3R)-3-Methoxy-2-((S)-3-methyl-2-methylamino-3-phenyl-butyrylamino)-butyryl]-methyl-amino}-2,5-dimethyl-hex-2-enoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.

8
[ 4144-02-9 ]
(E)-(S)-4-[((2S,3R)-2-Amino-3-methoxy-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester; hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.

9
[ 4144-02-9 ]
(E)-(S)-4-({(2S,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-methoxy-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.

10
[ 4144-02-9 ]
(E)-(S)-4-({(2S,3R)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-3-phenyl-butyrylamino]-3-methoxy-butyryl}-methyl-amino)-2,5-dimethyl-hex-2-enoic acid ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.

11
[ 2076-53-1 ]
[ 4144-02-9 ]

References: [1]Journal of Biological Chemistry,1937,vol. 119,p. 104,105.
Org.Synth.Coll.Vol.,1955,vol. III,p. 813.

12
[ 6622-23-7 ]
[ 4144-02-9 ]

References: [1]Journal of Biological Chemistry,1937,vol. 119,p. 104,105.
Org.Synth.Coll.Vol.,1955,vol. III,p. 813.

13
[ 4144-02-9 ]
[ 5405-44-7 ]

References: [1]Nippon Kagaku Zasshi,1950,vol. 71,p. 500.
Chem.Abstr.,1951,p. 9483.

14
N-Boc-L-Thr(Me)-OMe [ No CAS ]
[ 4144-02-9 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 5319 - 5327.
[2]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 6134 - 6143.

15
[ 4144-02-9 ]
[ 79-22-1 ]
[ 1007881-21-1 ]

Yield	Reaction Conditions	Operation in experiment
97%		To a mixture of 0-methyl -L-threonine (3.0 g, 22.55 mmol) , MaOH (0.902 g, 22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at O0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1HNMR (400 MHz, CDCl3) delta 4.19 (s, IH), 3.92-3.97 (m, IH), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H) . LCMS: Anal. Calcd. for C7Hi3NO5: 191; found: 190 (M-H)".
97%		To a mixture of O-methyl~L-threonine (3.0 g, 22.55 mmol), NaOH (0.902 g,22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at 00C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g? 97%) which was of sufficient purity for use in subsequent steps. 1H NMR (400 MHz, CDCl3) delta 4.19 (s, IH), 3.92-3.97 (m, IH)5 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)".
97%	With sodium hydroxide; In water; at 0℃; for 12.0h;	To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g,22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at O0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1H NMR (400 MHz, CDCl3) delta 4.19 (s, IH), 3.92-3.97 (m, IH), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)-.

97%		To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. XH NMR (400 MHz, CDC13) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)
97%		Cap-86 Me0(2S,3R)-3-Methoxy-2-(methoxycarbonylamino)butanoic acid[00213] To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2C12 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. XH NMR (400 MHz, CDC13) 5 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LC-MS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)".
97%	With sodium hydroxide; In water; at 0℃; for 12.0h;	To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1HNMR (400 MHz, CDC13) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)".
97%		To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at 00C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HCl. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1HNMR (400 MHz, CDCl3) delta 4.19 (s, IH), 3.92-3.97 (m, IH), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)".
		To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H2O (15 mL) was added ClCO2Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using 1N HCl. The aqueous phase was extracted with EtOAc and (2×250 mL) and 10% MeOH in CH2Cl2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1H NMR (400 MHz, CDCl3) delta4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J=7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13NO5: 191; found: 190 (M-H)-.
		To a mixture of <strong>[4144-02-9]O-methyl-L-threonine</strong> (3.0 g, 22.55 mmol), NaOH (0.902 g, 22.55 mmol) in H20 (15 mL) was added ClC02Me (1.74 mL, 22.55 mmol) dropwise at 0 C. The mixture was allowed to stir for 12 h and acidified to pH 1 using IN HC1. The aqueous phase was extracted with EtOAc and (2x250 mL) and 10% MeOH in CH2CI2 (250 mL) and the combined organic phases were concentrated under in vacuo to afford a colorless oil (4.18 g, 97%) which was of sufficient purity for use in subsequent steps. 1H NMPv (400 MHz, CDCI3) delta 4.19 (s, 1H), 3.92-3.97 (m, 1H), 3.66 (s, 3H), 1.17 (d, J = 7.7 Hz, 3H). LCMS: Anal. Calcd. for C7H13N05: 191; found: 190 (M-H)-.
		O-Methyl-L-threonine (25 g, 0.19 mol) was dissolved in 1,4-dioxane (125 mL) and cooled to 0 C. An aq 2 M NaOH (22.5 g, 0.56 mol, 3 equiv) solution was then added to the reaction mixture followed by methyl chloroformate (17.4 mL, 0.22 mol, 1.2 equiv) at the same temperature. The reaction mixture was warmed to rt and stirred for 16 h. The reaction mixture was washed with ethyl acetate (500 mL). The aq layer was acidified with 3 N HCl (up to pH 2) and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford the crude product (23 g). Ethyl acetate (46 mL) was added to the crude product and heated at 80 C. to obtain a clear solution. This solution was then cooled to 0 C. The solid obtained was filtered and dried to afford the desired pure product (21) (18.75 g).
	With sodium hydroxide; In water; at 20℃; for 12.0h;Sealed tube; Cooling with ice;	Weigh 3.0gO- methyl -L- threonineAnd 0.902 g of sodium hydroxideIn a 100 mL dry vial,15 mL of water was added,0 underAfter adding 1.74 mL of methyl chloroformate,It was stirred under ice-naturally warmed to room temperature,Reaction 12h,After completion of the reaction,The reaction solution was adjusted to pH 1 with 1N HCl solution,Ethyl acetate extraction (5 x 100 mL) was added,The organic phase was dried,filter,Concentrated to give the title compound,Directly for the next reaction.

References: [1]Patent: WO2010/120621,2010,A1 .Location in patent: Page/Page column 143.
[2]Patent: WO2010/138488,2010,A1 .Location in patent: Page/Page column 132.
[3]Patent: WO2010/138368,2010,A1 .Location in patent: Page/Page column 90.
[4]Patent: WO2011/60000,2011,A1 .Location in patent: Page/Page column 173.
[5]Patent: WO2011/75439,2011,A1 .Location in patent: Page/Page column 80-81.
[6]Patent: WO2012/18325,2012,A1 .Location in patent: Page/Page column 84.
[7]Patent: WO2008/144380,2008,A1 .Location in patent: Page/Page column 93-94.
[8]Journal of Medicinal Chemistry,2018,vol. 61,p. 4052 - 4066.
[9]Patent: US2009/233925,2009,A1 .Location in patent: Page/Page column 41-42.
[10]Patent: WO2011/59850,2011,A1 .Location in patent: Page/Page column 85-86.
[11]Patent: US2012/302538,2012,A1 .Location in patent: Page/Page column 21.
[12]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4106 - 4111.
[13]Patent: CN105985355,2016,A .Location in patent: Paragraph 0248; 0249; 0250; 0251.

16
[ 4144-02-9 ]
[ 139601-90-4 ]
C₁₄H₁₈FN₅O₇ [ No CAS ]

References: [1]Tetrahedron,2009,vol. 65,p. 10424 - 10429.

17
perthamide C [ No CAS ]
[ 107-97-1 ]
[ 4144-02-9 ]
[ 7423-92-9 ]
[ 6734-41-4 ]

References: [1]Tetrahedron,2009,vol. 65,p. 10424 - 10429.

18
perthamide C [ No CAS ]
[ 4144-02-9 ]
[ 56-84-8 ]
[ 5753-30-0 ]

References: [1]Tetrahedron,2009,vol. 65,p. 10424 - 10429.

19
perthamide D [ No CAS ]
[ 4144-02-9 ]
[ 56-84-8 ]
[ 63-91-2 ]
[ 5753-30-0 ]

References: [1]Tetrahedron,2009,vol. 65,p. 10424 - 10429.

20
[ 4144-02-9 ]
[ 1246891-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With diborane; In tetrahydrofuran; at 20 - 30℃; for 12.0h;	A solution of <strong>[4144-02-9](2S,3R)-2-amino-3-methoxybutanoic acid</strong> (1 g, 7.51 mmol, 1 equiv), diborane hydrogen (15.0 mL, 1 mol/L, 2 equiv) in THF (15 mL) was stirred for 12 h at RT. The reaction was quenched by the addition of 15 mL of methanol. The resulting mixture was diluted with 15 mL of water and washed with 2*30 ml of DCM. The organic layers were combined and dried over Na2SO4. The resulting mixture was concentrated to afford 2.2 g (crude) of the title compound as colorless oil. LCMS (ESI, m/z): 120.09 [M+H]+

References: [1]Tetrahedron,2010,vol. 66,p. 7707 - 7719.
[2]Patent: US2019/330194,2019,A1 .Location in patent: Paragraph 1922.

21
[ 4144-02-9 ]
[ 1007881-21-1 ]

Yield	Reaction Conditions	Operation in experiment
0.28 g (20%)		Example 51A (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid <strong>[4144-02-9](2S,3R)-2-amino-3-methoxybutanoic acid</strong> (1.0 g, 7.51 mmol) was processed as in Example 25A to give 0.28 g (20%) of the title compound as a waxy solid.

References: [1]Patent: US2010/267634,2010,A1 .

22
[ 4144-02-9 ]
methyl ((1S,2R)-2-methoxy-1-(((2S)-2-(4-(2'-(2-((2S)-1-(N-(methoxycarbonyl)-O-methyl-L-threonyl-)-2-pyrrolidinyl)-1H-imidazol-4-yl)-5,5'-bi-thiazol-2-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate trifluoroacetate [ No CAS ]

References: [1]Patent: WO2011/60000,2011,A1 .

23
[ 4144-02-9 ]
methyl ((1S,2R)-2-methoxy-1-(((2S)-2-(4-(5'-(2-((2S)-1-(N-(methoxycarbonyl)-O-methyl-L-threonyl-)-2-pyrrolidinyl)-1H-imidazol-4-yl)-2,2'-bi-1,3-thiazol-5-yl)-1H-imidazol-2-yl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamate trifluoroacetate [ No CAS ]

References: [1]Patent: WO2011/60000,2011,A1 .

24
[ 4144-02-9 ]
C₁₂H₁₆N₄O₅ [ No CAS ]
C₁₇H₂₅N₅O₈ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 6134 - 6143.

25
[ 4144-02-9 ]
[ 1415120-17-0 ]

References: [1]Patent: US2012/302538,2012,A1 .

26
[ 4144-02-9 ]
[ 1449473-62-4 ]