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

Base Information

• Chemical Name: 2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid
• CAS No.: 220662-80-6
• Molecular Formula: C₄₂H₄₂O₈
• Molecular Weight: 674.791
• Mol file: 220662-80-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid 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: 97.0%

carbon dioxide (124-38-9,18923-20-1) + 2-bromobenzyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (190508-15-7) → 2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid (220662-80-6)

Guidance literature:

2-bromobenzyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h;

carbon dioxide; In tetrahydrofuran; hexane; at -100 ℃; for 0.5h;

DOI:10.1021/jo971778e

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'-(benzyloxycarbonyl)benzyl β-D-glucopyranoside (365535-55-3) → 2-{[(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]methyl}benzoic acid (220662-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaH / dimethylformamide / 2 h / 20 °C

2: 94 percent / H₂; NH₄OAc / Pd/C / methanol / 1 h / 20 °C

With ammonium acetate; hydrogen; sodium hydride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.03.014

upstream raw materials:

carbon dioxide

2-bromobenzyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

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

benzyl bromide

Downstream raw materials:

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

methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

1,2-dimethyl-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-indole

methyl 6-{1-[2-(((2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy)methyl)phen-1-yl]vinyl}-2,3,4-tri-O-benzyl-α-D-glucopyranoside