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

Base Information

• Chemical Name: methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• CAS No.: 1260731-56-3
• Molecular Formula: C₅₅H₅₄O₁₄
• Molecular Weight: 939.025
• Mol file: 1260731-56-3.mol

Synonyms:methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Chemical Property of methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

There total 5 articles about methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-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: 75.0%

3,4,6-tri-O-benzyl-D-glucopyranose (20672-66-6,40246-26-2,84926-76-1,114179-79-2,115184-49-1) + methyl 2,3,4-tri-O-benzoyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside (187961-58-6) → methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside (1260731-56-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine; In acetonitrile; at 20 ℃; for 24h; stereoselective reaction; Molecular sieve;

DOI:10.1021/acs.orglett.8b03823

Reference yield: 53.0%

methyl 2,3,4-tri-O-benzoylglucopyranoside (34234-44-1) + C36H38O7S (1260731-50-7) → methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside (1260731-56-3)

Guidance literature:

C₃₆H₃₈O₇S; With 2,6-di-tert-butyl-4-methylpyridine; 1,2,3-trimethoxybenzene; In 1,2-dichloro-ethane; at 20 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In 1,2-dichloro-ethane; at -30 - -10 ℃; for 0.166667h; Inert atmosphere;

methyl 2,3,4-tri-O-benzoylglucopyranoside; optical yield given as %de; stereoselective reaction; Further stages;

DOI:10.1021/ol1027267

Reference yield:

1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose (53270-12-5) → methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside (1260731-56-3)

Guidance literature:

Multi-step reaction with 2 steps

1: water / 24 h / Reflux

2: 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine; N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / 20 °C / Molecular sieve

With N-ethyl-N,N-diisopropylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine; In water; acetonitrile;

DOI:10.1021/acs.orglett.8b03823

upstream raw materials:

methyl 2,3,4-tri-O-benzoylglucopyranoside

C₃₆H₃₈O₇S

3,4,6-tri-O-benzyl-D-glucopyranose

methyl 2,3,4-tri-O-benzoyl-6-O-trifluoromethanesulfonyl-α-D-glucopyranoside