methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Base Information

• Chemical Name: methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside
• CAS No.: 1467030-42-7
• Molecular Formula: C₅₁H₈₃NO₁₂Si₃
• Molecular Weight: 986.476
• Mol file: 1467030-42-7.mol

Synonyms:methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Chemical Property of methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

There total 1 articles about methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside 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: 57.0%

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1300080-67-4) + C38H66O7S2Si3 → methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1467030-42-7)

Guidance literature:

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside; C₃₈H₆₆O₇S₂Si₃; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -50 ℃; for 0.916667h; regioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2013.08.002

Reference yield:

methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1467030-42-7) → C33H41NO12

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; ethyl acetate; at -20 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1016/j.carres.2013.08.002

Reference yield:

methyl 6-O-benzyl-2,3,4-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside (1467030-42-7) → C41H49NO16 (1467030-57-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; ethyl acetate / 17 h / -20 - 20 °C / Inert atmosphere

2: pyridine; dmap / 20 °C / Inert atmosphere

With pyridine; dmap; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/j.carres.2013.08.002

upstream raw materials:

methyl 6-O-benzyl-2-deoxy-2-dimethylmaleimido-α-D-allopyranoside

Downstream raw materials:

C₄₁H₄₉NO₁₆