(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

Base Information

• Chemical Name: (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside
• CAS No.: 1357376-77-2
• Molecular Formula: C₃₃H₄₉ClO₈Si
• Molecular Weight: 637.286
• Mol file: 1357376-77-2.mol

Synonyms:(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

Chemical Property of (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

There total 3 articles about (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-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:

4-chlorobutyl bromide (6940-78-9) + tert-butylchlorodiphenylsilane (58479-61-1) + (2'R,3'R)-methyl 2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (176798-28-0) → (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357376-77-2)

Guidance literature:

4-chlorobutyl bromide; (2'R,3'R)-methyl 2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside; With sodium hydroxide; In water; dimethyl sulfoxide; at 20 ℃; for 20h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.carres.2011.08.024

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357376-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: camphor-10-sulfonic acid / methanol

2.1: sodium hydroxide / water; dimethyl sulfoxide / 20 h / 20 °C

2.2: 20 °C

With camphor-10-sulfonic acid; sodium hydroxide; In methanol; water; dimethyl sulfoxide; 2.1: Williamson synthesis;

DOI:10.1016/j.carres.2011.08.024

Reference yield:

(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357377-06-0) → (2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-chlorobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357376-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C

2.1: sodium hydroxide / water; dimethyl sulfoxide / 20 h / 20 °C

2.2: 20 °C

With tetrabutyl ammonium fluoride; sodium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide; 2.1: Williamson synthesis;

DOI:10.1016/j.carres.2011.08.024

upstream raw materials:

4-chlorobutyl bromide

tert-butylchlorodiphenylsilane

(2'R,3'R)-methyl 2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

Downstream raw materials:

(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(4''-iodobutyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

(2'R,3'R)-methyl 6-O-tert-butyldiphenylsilyl-4-O-(5'',5''-di-tert-butoxycarbonylpentyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside