4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester

Base Information

• Chemical Name: 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester
• CAS No.: 78880-57-6
• Molecular Formula: C₄₇H₄₄O₈
• Molecular Weight: 736.862

Synonyms:4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester

Chemical Property of 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester

Chemical Property:

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Technology Process of 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester

There total 2 articles about 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + Phenyl 4-hydroxybenzoate (17696-62-7) → 4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester (78880-57-6) + 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester (78880-57-6)

Guidance literature:

With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride; Multistep reaction; 1.) CH₂Cl₂, -10 deg C, 0.5 h, 2.) CH₂Cl₂, 0 deg C, 3 h;

DOI:10.1246/bcsj.54.1895

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + Phenyl 4-hydroxybenzoate (17696-62-7) → 4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester (78880-57-6) + 4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester (78880-57-6)

Guidance literature:

With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride; Multistep reaction; 1.) CH₂Cl₂, -10 deg C, 0.5 h, 2.) CH₂Cl₂, 0 deg C, 3 h;

DOI:10.1246/bcsj.54.1895

Reference yield: 84.0%

4-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid phenyl ester (78880-57-6) → 4-(phenoxycarbonyl)phenyl-α-D-glucopyranoside (78880-60-1)

Guidance literature:

With hydrogen; palladium; In methanol; water; acetic acid; under 2550.2 Torr;

DOI:10.1246/bcsj.54.1895

upstream raw materials:

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

Phenyl 4-hydroxybenzoate

Downstream raw materials:

4-(phenoxycarbonyl)phenyl-α-D-glucopyranoside

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