(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

Base Information

• Chemical Name: (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
• CAS No.: 1357376-79-4
• Molecular Formula: C₄₄H₆₈O₁₂Si
• Molecular Weight: 817.102
• Mol file: 1357376-79-4.mol

Synonyms:(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

Chemical Property of (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

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-(5'',5''-di-tert-butoxycarbonylpentyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside

There total 6 articles about (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 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: 26.0%

t-butyl malonate (541-16-2) + (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 (1357376-78-3) → (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 (1357376-79-4)

Guidance literature:

t-butyl malonate; With potassium tert-butylate; In tetrahydrofuran; Inert atmosphere; Reflux;

(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; In tetrahydrofuran; Inert atmosphere; Reflux;

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-(5'',5''-di-tert-butoxycarbonylpentyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357376-79-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: camphor-10-sulfonic acid / methanol

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

2.2: 20 °C

3.1: sodium iodide / acetone / 24 h / Reflux

4.1: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux

4.2: Inert atmosphere; Reflux

With camphor-10-sulfonic acid; potassium tert-butylate; sodium iodide; sodium hydroxide; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; acetone; 2.1: Williamson synthesis / 3.1: Finkelstein reaction;

DOI:10.1016/j.carres.2011.08.024

Reference yield:

(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-(5'',5''-di-tert-butoxycarbonylpentyl)-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-glucopyranoside (1357376-79-4)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 20 °C

2.1: sodium iodide / acetone / 24 h / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux

3.2: Inert atmosphere; Reflux

With potassium tert-butylate; sodium iodide; sodium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide; acetone; 1.1: Williamson synthesis / 2.1: Finkelstein reaction;

DOI:10.1016/j.carres.2011.08.024

upstream raw materials:

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

(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

t-butyl malonate

(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