phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide
• CAS No.: 1138123-66-6
• Molecular Formula: C₂₁H₂₄Cl₃NO₁₀S
• Molecular Weight: 588.847
• Mol file: 1138123-66-6.mol

Synonyms:phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide

Chemical Property of phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide

There total 3 articles about phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide 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: 98.0%

(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate (187022-49-7) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide (1138123-66-6)

Guidance literature:

With Selectfluor; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/ja4000933

Reference yield:

thiophenol (108-98-5) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide (1138123-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 4 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -80 °C

With trimethylsilyl trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo102411j

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside S-oxide (1138123-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 4 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / -80 °C

With trimethylsilyl trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo102411j

upstream raw materials:

(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)-5-(((2,2,2-trichloroethoxy)carbonyl)amino)tetrahydro-2H-pyran-3,4-diyl diacetate

thiophenol

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

Downstream raw materials:

C₃₅H₄₂Cl₆N₂O₁₈S

C₃₆H₄₆Cl₆N₂O₁₇S

C₄₂H₄₄Cl₃NO₁₈

C₄₂H₄₆Cl₃NO₁₈