2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

Base Information

• Chemical Name: 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride
• CAS No.: 138857-92-8
• Molecular Formula: C₂₄H₂₃ClO₉
• Molecular Weight: 490.894
• Mol file: 138857-92-8.mol

Synonyms:2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

Chemical Property of 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride

There total 5 articles about 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride 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: 83.0%

methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside (138857-75-7) → 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride (138857-92-8)

Guidance literature:

With Dichloromethyl methyl ether; zinc(II) chloride; In chloroform; at 65 ℃; for 11h;

DOI:10.1016/0008-6215(94)80063-4

Reference yield: 64.0%

1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose (138857-85-9) → 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride (138857-92-8)

Guidance literature:

With Dichloromethyl methyl ether; zinc(II) chloride; In chloroform; at 60 ℃; for 1h;

Reference yield:

methyl 2,3-bis-O-benzoyl-α-D-galactopyranoside (4137-35-3) → 2,3-di-O-benzoyl-4,6-O-<1-(R)-methoxycarbonyl(ethylidene)>-α-D-galactopyranosyl chloride (138857-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / BF₃*Et₂O / acetonitrile / 2.5 h / Ambient temperature

2: 83 percent / dichloromethyl methyl ether, ZnCl₂ / CHCl₃ / 11 h / 65 °C

With Dichloromethyl methyl ether; boron trifluoride diethyl etherate; zinc(II) chloride; In chloroform; acetonitrile;

DOI:10.1016/0008-6215(94)80063-4

upstream raw materials:

pyruvic acid methyl ester

phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside

methyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside

1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose

Downstream raw materials:

methyl O-<(R)-2,3-di-O-benzoyl-4,6-O-(1-methoxycarbonylethylidene)-β-D-galactopyranosyl>-(1-3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside

benzyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-β-D-galactopyranosyl>-(1<*>3)-2-O-benzoyl-4,6-O-<(S)-1-(methoxycarbonyl)ethylidene>-α-D-glucopyranoside

benzyl O-<2,3-di-O-benzoyl-4,6-O-<(R)-1-(methoxycarbonyl)ethylidene>-α-D-galactopyranosyl>-(1<*>3)-2-O-benzoyl-4,6-O-<(S)-1-(methoxycarbonyl)ethylidene>-α-D-glucopyranoside

1,2,3-tri-O-benzoyl-4,6-O-<(R)-1-methoxycarbonyl(ethylidene)>-α-D-galactopyranose