phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• CAS No.: 1225199-04-1
• Molecular Formula: C₂₄H₂₆Cl₃NO₇S
• Molecular Weight: 578.898
• Mol file: 1225199-04-1.mol

Synonyms:phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Chemical Property of phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 5 articles about phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 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: 85.0%

phenyl 3-O-acetyl-4,6-benzylidene-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside (1225199-03-0) → phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1225199-04-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;

DOI:10.1039/b926177j

Reference yield: 82.0%

phenyl 3-O-acetyl-2-deoxy-4,6-O-benzylidene-1-thio-2-[(2,2,2-trichloroethoxy)carbonyl]amino-β-D-glucopyranoside → phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1225199-04-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02791

Reference yield:

phenyl 2-[(2,2,2-trichloroethoxy)carbonyl]amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside (371123-28-3) → phenyl 3-O-acetyl-2-deoxy-6-O-benzyl-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1225199-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 18 h / 20 °C / Inert atmosphere

2: triethylsilane; copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 0 - 20 °C / Inert atmosphere

With triethylsilane; copper(II) bis(trifluoromethanesulfonate); In acetonitrile;

DOI:10.1002/adsc.201100228

upstream raw materials:

phenyl 3-O-acetyl-4,6-benzylidene-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranoside

phenyl 2-[(2,2,2-trichloroethoxy)carbonyl]amino-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside

benzaldehyde dimethyl acetal

phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 6-O-(3-O-acetyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl-amino)-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside