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

Base Information

• Chemical Name: 2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester
• CAS No.: 688800-59-1
• Molecular Formula: C₄₉H₄₈O₈
• Molecular Weight: 764.915
• Mol file: 688800-59-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl 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: 80.0%

benzyl bromide (100-39-0) + 2'-(benzyloxycarbonyl)benzyl β-D-glucopyranoside (365535-55-3) → 2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester (688800-59-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2006.03.014

Reference yield: 94.0%

2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester (688800-59-1) → 2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid (220662-80-6)

Guidance literature:

With ammonium acetate; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2006.03.014

Reference yield:

2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid benzyl ester (688800-59-1) → 2-((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzoic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / H₂; NH₄OAc / Pd/C / methanol / 1 h / 20 °C

2.1: 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 20 °C

2.2: Tf₂O / CH₂Cl₂ / 0.17 h / -78 °C

2.3: 39 percent / CH₂Cl₂ / 2 h / -78 - 0 °C

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; ammonium acetate; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.carres.2006.03.014

upstream raw materials:

benzyl bromide

2'-(benzyloxycarbonyl)benzyl β-D-glucopyranoside

Downstream raw materials:

2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose

1-(2,3,4,6-O-tetrabenzyl-α-D-glucopyranosyl)-2-propene

α1-deoxy-1-(C-2',4'-dimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose