beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Chemical Properties

Melting point:

128-130 °C

alpha 

24.4 º (c=1, pyridine)

Boiling point:

621.0±55.0 °C(Predicted)

Density 

1.35±0.1 g/cm3(Predicted)

refractive index 

24 ° (C=1, Pyridine)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated),

form 

Liquid

color 

Clear slightly yellow or greenish to brown

optical activity

[α]20/D +24.3°, c = 1 in pyridine

BRN 

100243

InChI

InChI=1/C28H24O9/c1-17(29)34-28-24(36-26(31)19-13-7-4-8-14-19)23(35-25(30)18-11-5-3-6-12-18)22(37-28)20-15-9-10-16-21(20)27(32)33-2/h3-16,22-24,28H,1-2H3/t22-,23-,24-,28-/s3

InChIKey

GCZABPLTDYVJMP-CBUXHAPBSA-N

SMILES

C(OC)(=O)C1=CC=CC=C1[C@@H]1[C@@H](OC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](OC(C)=O)O1 |&1:10,11,21,31,r|

CAS DataBase Reference

6974-32-9(CAS DataBase Reference)

EPA Substance Registry System

.beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate (6974-32-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29400090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion

Application

Beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, also known as 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, is a ribose-derived compound used in nucleoside synthesis.

Synthesis

Rac-(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-hydroxytetrahydrofuran-3,4-diyl dibenzoate was dissolved in dry pyridine, and the solution was slowly added dropwise with acetic anhydride in an ice water bath, then stirred for 30 minutes. Then, the ice water bath was removed, and the solution was stirred at room temperature for 7 hours and then heated to 40°C. This temperature was kept for an hour. The solution was added with broken ice and then stirred until the broken ice melted. The reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed sequentially with ice water, pre-cooled sulfuric acid, and saturated sodium bicarbonate until the water layer showed weak alkaline, then washed with ice water until the water layer showed neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under reduced pressure, to obtain the light yellow syrup-like beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate (92.1%).

Purification Methods

Recrystallise it from EtOH or isoPrOH. [Helv Chim Acta 42 1171 1959, NMR: J Org Chem 33 1799 1968, IR: Chem Pharm Bull Jpn 11 188 1963, Beilstein 17/6 V 213.]

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