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

Base Information

• Chemical Name: phenyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside
• CAS No.: 154391-09-0
• Molecular Formula: C₃₀H₂₈O₉S
• Molecular Weight: 564.613
• Mol file: 154391-09-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about phenyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside 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:

pyruvic acid methyl ester (600-22-6) + phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside (138857-53-1) → phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside (138857-83-7) + phenyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside (154391-09-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 24h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)60097-7

Reference yield: 85.0%

phenyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside (154391-09-0) → 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranosyl fluoride (154391-13-6)

Guidance literature:

With N-Bromosuccinimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -15 ℃; for 15h;

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

Reference yield:

phenyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-1-thio-α-D-galactopyranoside (154391-09-0) → ethyl 2,3-di-O-benzoyl-4,6-O<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DAST, NBS / CH₂Cl₂ / 15 h / -15 °C

2: 10 percent / 5-<(benzyloxycarbonyl)amino>pentanol, Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With N-Bromosuccinimide; 5-<(benzyloxycarbonyl)amino>pentanol; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

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

Downstream raw materials:

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

5-<(benzyloxycarbonyl)amino>pentyl 2,3-di-O-benzoyl-4,6-O<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside