(2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside

Base Information

• Chemical Name: (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside
• CAS No.: 741735-03-5
• Molecular Formula: C₂₁H₃₂O₈
• Molecular Weight: 412.48
• Mol file: 741735-03-5.mol

Synonyms:(2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside

Chemical Property of (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside

There total 1 articles about (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside 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:

((2S,3S,4aR,5R,7S,8S,8aS)-8-Benzyloxy-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl)-methanol → (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside (741735-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; triethylamine; DMSO / tetrahydrofuran / -60 - 20 °C

2: 2.6 g / toluene; tetrahydrofuran / 2 h / -60 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; toluene; 1: Swern oxidation;

DOI:10.1021/ja0485659

Reference yield: 67.0%

(S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) + (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside (741735-03-5) → (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-((2S,3S,4aR,5R,7S,8S,8aS)-8-benzyloxy-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl)-ethyl ester

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja0485659

Reference yield: 56.0%

R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) + (2'S,3'S)-methyl 2-O-benzyl-7-deoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-L-glycero-α-D-manno-heptapyranoside (741735-03-5) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-((2S,3S,4aR,5R,7S,8S,8aS)-8-benzyloxy-2,3,7-trimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl)-ethyl ester

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ja0485659