2,3,4,6-Tetra-O-benzyl-D-glucopyranose

CAS: 4132-28-9

Ref. 3D-T-1900

Product Information

• Name: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
• Synonyms: (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol, 2,3,4,6-Tetra-O-benzoyl-<span class="text-smallcaps">D</span>-glucopyranose, 2,3,4,6-Tetra-O-benzyl-D-glucofuranose, 2,3,4,6-Tetra-O-benzyl-alpha-D-glucose, 2,3,4,6-Tetra-O-benzyl-glucopyranose, 2,3,4,6-Tetrakis-O-(phenylmethyl)-<span class="text-smallcaps">D</span>-glucopyranose, <span class="text-smallcaps">D</span>-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-, Glucopyranose, 2,3,4,6-tetra-O-benzyl-, Glucopyranose, 2,3,4,6-tetra-O-benzyl-, <span class="text-smallcaps">D</span>-

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 α-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.

• Brand: Biosynth

Chemical properties

• Molecular weight: 540.66 g/mol
• Formula: C₃₄H₃₆O₆
• Purity: Min. 98.0 Area-%