2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose , 98% , 6564-72-3

CAS NO.：6564-72-3

Empirical Formula: C34H36O6

Molecular Weight: 540.66

MDL number: MFCD00066004

EINECS: 667-304-9

PRODUCT 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)

Description and Uses

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.

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.

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H315-H319
• Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
• Safety Statements: 22-24/25
• WGK Germany: 3