2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Chemical Properties

Melting point:

151-156 °C

Boiling point:

672.4±55.0 °C(Predicted)

Density 

1.22

storage temp. 

Sealed in dry,Store in freezer, under -20°C

pka

11.87±0.70(Predicted)

Water Solubility 

Soluble in CHCl3. Insoluble in water.

LogP

5.9 at 20℃ and pH6.5

CAS DataBase Reference

6564-72-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE Usage And Synthesis

Description

2,3,4,6-Tetra-O-benzyl-D-glucopyranose is a selectively protected intermediate, where the anomeric 1-O-hydroxyl group is free. This hemiacetal has been used successfully as an intermediate for glucosylation couplings, where it was converted into 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate using trichloroacetonitrile in the presence of a base such as potassium carbonate and DBU.
Importantly, this imidate donor with no neighbouring participating groups is commonly used for the selective formation of glucosides. 2,3,4,6-tetra-O-benzyl-D-glucopyranose can also be oxidized to the lactone, or reduced to give the open chain form.
Additionally, 2,3,4,6-tetra-O-benzyl-D-glucopyranose can be used for the preparation of glucono-1,5-lactone hydrazine, which was used, in-turn, to form a glucosylidene-spirocyclopropane.

Uses

It is the intermediate of Voglibose/Dapagliflozin. An important D-glucopyranose derivative for glucosylations and other reactions 1,2; Preparation of the α-glucopyranosyl chloride, synthesis of 1-C-α-D-glucopyranose derivatives.

Synthesis

Octa-O-Dissolves benzyl sucrose or octa-O-allyl sucrose in an organic solvent with the addition of hydrochloric acid without prior chromatographic purification, allows it to react for 20-60 minutes at temperatures of 50-60 °C. and then cleans the end product formed by crystallization. (ethanol, isopropanol, acetone, benzene, toluene or mixtures thereof can be used as solvents).

2,3,4,6-TETRA-O-BENZYL-ALPHA-D-GLUCOPYRANOSE(6564-72-3)Related Product Information

• (S)-Valiolamine Voglibose
• Valiolamine
• (2S,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylMethoxy)-5-[(phenylMethoxy)Methyl]-cyclohexanone
• (R)-Valiolamine Voglibose
• ETHYL 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-THIOGLUCOPYRANOSIDE
• Methyl-2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside
• 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE
• Methyl beta-D-ribofuranoside
• 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE
• 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranosyl azide 3,4,6-Triacetate
• FMOC-SER(GALNAC(AC)3-ALPHA-D)-OH
• Penta-O-benzoyl-alpha-D-mannopyranose
• 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-α-D-glucopyranosyl azide 3,4,6-Triacetate
• FMOC-THR(GALNAC(AC)3-ALPHA-D)-OH
• D-Galactose
• 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
• 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide
• 2,3,4,6-Tetra-O-benzyl-D-glucopyranose