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

Base Information

• Chemical Name: 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide
• CAS No.: 154460-38-5
• Molecular Formula: C₂₄H₂₃BrO₉
• Molecular Weight: 535.345
• Mol file: 154460-38-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide 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: 53.0%

phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside (138857-83-7) → 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide (154460-38-5)

Guidance literature:

With bromine; In dichloromethane; for 2h; Ambient temperature;

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

Reference yield:

phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside (138857-53-1) → 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide (154460-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / BF₃*Et₂O / acetonitrile / 2.5 h / Ambient temperature

2: 53 percent / Br₂ / CH₂Cl₂ / 2 h / Ambient temperature

With boron trifluoride diethyl etherate; bromine; In dichloromethane; acetonitrile;

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

Reference yield: 71.0%

5-<(benzyloxycarbonyl)amino>pentanol (87905-98-4) + 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide (154460-38-5) → 5-<(benzyloxycarbonyl)amino>pentyl 2,3-di-O-benzoyl-4,6-O<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside (154391-16-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; for 0.25h; Ambient temperature;

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

upstream raw materials:

phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside

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

Downstream raw materials:

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