methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside
• CAS No.: 629627-31-2
• Molecular Formula: C₄₂H₄₆O₁₁
• Molecular Weight: 726.821

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

There total 2 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 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:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + phenyl 2-O-benzyl-3,4-O-carbonyl-1-thio-β-L-rhamnopyranoside (629627-27-6) → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (629627-31-2) + methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-β-L-rhamnopyranosyl)-α-D-glucopyranoside

Guidance literature:

phenyl 2-O-benzyl-3,4-O-carbonyl-1-thio-β-L-rhamnopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.333333h;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; In dichloromethane; at -60 ℃; for 1h;

DOI:10.1021/jo035003j

Reference yield:

phenyl 2-O-benzyl-1-thio-β-L-rhamnopyranoside (629627-26-5) → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (629627-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 81 percent / 4-dimethylaminopyridine / CH₂Cl₂; toluene / 0.5 h / cooling

2.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / 0.33 h / -60 °C

2.2: CH₂Cl₂ / 1 h / -60 °C

With dmap; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; toluene;

DOI:10.1021/jo035003j

Reference yield: 68.0%

methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-3,4-O-carbonyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (629627-31-2) → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 3h;

DOI:10.1021/jo035003j

upstream raw materials:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

phenyl 2-O-benzyl-3,4-O-carbonyl-1-thio-β-L-rhamnopyranoside

phenyl 2-O-benzyl-1-thio-β-L-rhamnopyranoside

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