methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside
• CAS No.: 20272-21-3
• Molecular Formula: C₂₉H₂₅NO₈S
• Molecular Weight: 547.585
• Mol file: 20272-21-3.mol

Synonyms:methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside

There total 6 articles about methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-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: 72.5%

methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside (19467-77-7) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside (20272-21-3)

Guidance literature:

With potassium thioacyanate; In N,N-dimethyl-formamide; at 110 ℃; for 48h; also in the presence of 18-crown-6, the other time;

DOI:10.1021/jo00269a025

Reference yield:

methyl 2,3,6-tri-O-benzoyl-4-O-<(4-bromophenyl)sulfonyl>-α-D-glucopyranoside (57784-05-1) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside (20272-21-3)

Guidance literature:

With potassium thioacyanate; In N,N-dimethyl-formamide; at 110 ℃; for 17h; Yield given;

DOI:10.1021/jo00269a025

Reference yield:

1-benzoylimidazole (10364-94-0) → methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyano-α-D-galactopyranoside (20272-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) pyridine / 1.) MeCN, reflux, 24 h, 2.) 48 h, in the refrigerator

2: 72.5 percent / potassium thiocyanate / dimethylformamide / 48 h / 110 °C / also in the presence of 18-crown-6, the other time

With pyridine; potassium thioacyanate; In N,N-dimethyl-formamide;

DOI:10.1021/jo00269a025

upstream raw materials:

methyl 2,3,6-tri-O-benzoyl-4-O-<(4-bromophenyl)sulfonyl>-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside

1-benzoylimidazole

Downstream raw materials:

methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside

methyl 2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside