1,3,5-Tri-O-benzoyl-D-ribofuranose Chemical Properties

Melting point:

125-129 °C(lit.)

Boiling point:

629.6±55.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Powder

pka

12.35±0.70(Predicted)

color 

Pale brown

optical activity

[α]20/D +85.0°, c = 1 in chloroform

Water Solubility 

Insoluble in water, easily soluble in chloroform.

λmax

273nm(MeOH)(lit.)

BRN 

98446

InChIKey

HUHVPBKTTFVAQF-QFBXJQHPSA-N

SMILES

O(C(=O)C1=CC=CC=C1)C1O[C@H](COC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)[C@H]1O |&1:11,22,32,r|

CAS DataBase Reference

22224-41-5(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29400090

MSDS

• Language:English Provider:SigmaAldrich

1,3,5-Tri-O-benzoyl-D-ribofuranose Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

It is employed as a starting material for nucleosides and is an intermediate fir cloforabine.

Uses

Starting material for nucleosides.

Synthesis

Synthesis of compound vi: Compound v (2.57 mmol) was dissolved in 26 mL of anhydrous dichloromethane, and the reaction lasted for 2.5 h under the condition of ice-water bath with slow passage of dry HCl gas. After completion of the reaction, the reaction solution was washed with 19.5 mL of ice water and the organic layer was separated. The organic layer was washed sequentially with saturated sodium bicarbonate solution until the aqueous layer was weakly basic, and then washed with ice water until the aqueous layer was neutral. The organic layer was dried with anhydrous sodium sulfate for more than 4 hours and subsequently concentrated under reduced pressure to give a light yellow syrupy product. The syrup was recrystallized using a solvent mixture of hexane and dichloromethane to give the white solid compound vi in 65.1% yield.1H NMR (CDCl3) δ ppm: 7.36-8.14 (m, 15H, OBz), 6.68 (d, J = 4.4 Hz, 1H, H-1), 5.59 (dd, 1H, H-3), 4.64-4.80 ( m, 4H, H-2, H-4 and H-5). Melting point: 139-140°C.

References

[1] Patent: EP2177527, 2010, A1. Location in patent: Page/Page column 11
[2] Journal of Organic Chemistry, 1985, vol. 50, # 14, p. 2597 - 2598

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