methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 1309355-96-1
• Molecular Formula: C₄₁H₄₆O₉
• Molecular Weight: 682.811
• Mol file: 1309355-96-1.mol

Synonyms:

Chemical Property of methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

There total 7 articles about methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-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:

C27H30O6S + C21H23O6(1-)*K(1+) (1588522-56-8) → methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (1309355-96-1)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃; for 18h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja500410c

Reference yield:

p-methylphenyl 3,4-di-O-benzyl-2,6-dideoxy-1-thio-D-glucopyranoside + methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → methyl (3,4-di-O-benzyl-2,6-dideoxy-α-L-glucopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-α-D-glucopyranoside (1309355-95-0) + methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (1309355-96-1)

Guidance literature:

p-methylphenyl 3,4-di-O-benzyl-2,6-dideoxy-1-thio-D-glucopyranoside; With silver trifluoromethanesulfonate; In dichloromethane; at -70 ℃; for 1h; Molecular sieve; Inert atmosphere;

With p-methylbenzenesulfenyl chloride; In dichloromethane; at -70 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside; In dichloromethane; at -70 ℃; Overall yield = 88 percent; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.202013909

Reference yield:

(4S,5S,6S)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol → methyl (3,4-di-O-benzyl-2,6-dideoxy-β-L-arabinohexopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (1309355-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-tri-tert-butylpyrimidine; potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

With potassium hexamethylsilazane; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran;

DOI:10.1021/ja500410c

upstream raw materials:

C₂₁H₂₃O₆^(1-)*K⁽¹⁺⁾

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

benzyl bromide

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside