| Identification | More | [Name]
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE | [CAS]
6564-72-3 | [Synonyms]
2,3,4,6-TETRA-O-BENZOYL-D-GLUCOPYRANOSE
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE
2,3,4,6-Tetra-o-benzyl-D-glucopyransoe
2,3,4,6-Tetra-O-benzyl-a-D-glucopyranose
2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE ,GB
2,3,4,6-TETRA-O-ACETYL A-D-GLUCOPYRANOSIDE
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranos | [EINECS(EC#)]
667-304-9 | [Molecular Formula]
C34H36O6 | [MDL Number]
MFCD00066004 | [Molecular Weight]
540.65 | [MOL File]
6564-72-3.mol |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
|
| Hazard Information | Back Directory | [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). |
|
|