| Identification | More | [Name]
beta-D-Ribofuranose 1,2,3,5-tetraacetate | [CAS]
13035-61-5 | [Synonyms]
1,2,3,5-TETRAACETYL-B-D-RIBOFURANOSE
1,2,3,5-TETRAACETYL-BETA-D-RIBOFURANOSE
1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE
1,2,3,5-Tetra-O-acetyl-D-ribofuranose
BETA-D-RIBOFURANOSE 1,2,3,5-TETRAACETATE
BETA-D-RIBOFURANOSE 1,2,3,5-TETRA-O-ACETATE
BETA-D-RIBOFURANOSE TETRAACETATE
BETA(R)-D-TETRAACETYL RIBOSE
RIBOFURANOSE TETRAACETATE
TETRAACETYL-BETA-D-RIBOFURANOSE
TETRAACETYLRIBOFURANOSE
TETRAACETYLRIBOSE
TETRA-O-ACETYL-B-D-RIBOFURANOSE
TETRA-O-ACETYL-BETA-D-RIBOFURANOSE
1,2,3,5-tetraacetyl-beta-d-furanoribose
1,2,3,5-Tetraacetyl-beta-D-ribose
Tetra-O-ribofuranose
B-D-Ribofuranose 1,2,3,5-Tetraacetate
Ribose tetracetate
Tetra-O-acetyl-Ribose | [EINECS(EC#)]
235-898-5 | [Molecular Formula]
C13H18O9 | [MDL Number]
MFCD00005358 | [Molecular Weight]
318.28 | [MOL File]
13035-61-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to almost white crystalline powder | [Melting point ]
81-83 °C(lit.)
| [alpha ]
-15.4 º (c=7, MeOH) | [Boiling point ]
417.45°C (rough estimate) | [density ]
1.4171 (rough estimate) | [refractive index ]
-14.5 ° (C=5, MeOH) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Crystalline Powder | [color ]
White to almost white | [optical activity]
[α]26/D 11.4°, c = 10 in chloroform | [BRN ]
94078 | [InChI]
InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/s3 | [InChIKey]
TTXVPMATRDJQIA-BKUVIOGVSA-N | [SMILES]
[C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H]1OC(=O)C |&1:0,5,12,17,r| | [CAS DataBase Reference]
13035-61-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29400000 |
| Hazard Information | Back Directory | [Description]
beta-D-Ribofuranose 1,2,3,5-tetraacetate is an acetylated derivative of ribose extensively used in carbohydrate research and synthetic chemistry. This compound features acetyl groups protecting the hydroxyl functionalities at positions 1, 2, 3, and 5 of the ribofuranose ring, which enhances its stability and solubility in organic solvents. β-D-Ribofuranose 1,2,3,5-tetraacetate is a crucial intermediate in synthesising nucleosides, nucleotides, and other complex carbohydrates. In research, it is utilized to study glycosylation mechanisms, focusing on the formation and stereochemistry of glycosidic bonds.
| [Chemical Properties]
beta-D-Ribofuranose 1,2,3,5-tetraacetate is white to almost white crystalline powder
| [Uses]
beta-D-Ribofuranose 1,2,3,5-tetraacetate is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
| [Application]
beta-D-Ribofuranose 1,2,3,5-tetraacetate, also known as 1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranose (TAR), is an important organic reagent that can be used in the following pathways:
(1) Used in low-energy electron-induced reactions in gas-phase TAR. Since the acetyl group in TAR is coupled to the five-membered ribose ring at relevant positions, it can serve as a suitable model compound for studying the reaction of sugar units in DNA to low-energy electrons[1].
(2) Used to prepare 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic deacetylation[2].
(3) Used in condensation reactions. In the presence of tin chloride, 1-hexene reacts with 1- O -acetyl-2,3,5-tri- O -benzoyl-β- d -ribofuranose ( 5b ) or 1,2,3,5-tetra- O -acetyl-β- d -ribofuranose ( 5a ) to form a complex mixture[3]. | [References]
[1] ILKO BALD. Low energy electron-induced reactions in gas phase 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose: a model system for the behavior of sugar in DNA.[J]. Journal of Chemical Physics, 2007. DOI:10.1063/1.2436873.
[2] TUN-CHENG CHIEN; Ji W C. A convenient preparation of 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic regioselective 5-O-deacetylation of the peracetylated ribofuranose[J]. Carbohydrate Research, 2004. DOI:10.1016/j.carres.2004.01.010.
[3] THOMAS L. CUPPS; Leroy B T; Dean S Wise. A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-β-d-ribofuranoses[J]. Carbohydrate Research, 1983. DOI:10.1016/0008-6215(83)88135-X.
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| Spectrum Detail | Back Directory | [Spectrum Detail]
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)MS
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)1HNMR
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)13CNMR
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)IR1
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)IR2
beta-D-Ribofuranose 1,2,3,5-tetraacetate(13035-61-5)Raman
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