methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside
• CAS No.: 1186009-49-3
• Molecular Formula: C₄₉H₅₂O₁₂
• Molecular Weight: 832.945
• Mol file: 1186009-49-3.mol

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside

There total 8 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-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: 99.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + C23H22Cl3NO7 (1186009-20-0) → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside (1186009-49-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 20 ℃; Molecular sieve;

DOI:10.1016/j.bmcl.2009.03.155

Reference yield: 93.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 4-methylphenyl 2-O-benzoyl-4,6-O-benzylidine-3-O-methyl-1-thio-α-L-idopyranoside → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside (1186009-49-3)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 0.583333h; Molecular sieve; Inert atmosphere;

DOI:10.1021/jacs.9b03266

Reference yield:

4-methylphenyl 4-O-(4,6-O-benzylidine-2,3-di-O-methyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside → methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside (1186009-49-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C

3: acetic acid / water / 3 h / 70 °C

4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h / 0 - 20 °C

5: (R)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

6: pyridine / 12 h / 0 - 20 °C

7: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 0.58 h / -20 - 0 °C / Molecular sieve; Inert atmosphere

With pyridine; 1H-imidazole; N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; (R)-10-camphorsulfonic acid; sodium hydride; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1021/jacs.9b03266

upstream raw materials:

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

C₂₃H₂₂Cl₃NO₇

Downstream raw materials:

C₄₂H₄₈O₁₁

methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside