phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• CAS No.: 1283073-40-4
• Molecular Formula: C₂₈H₃₄Cl₃NO₁₀S₂
• Molecular Weight: 715.07
• Mol file: 1283073-40-4.mol

Synonyms:phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Chemical Property of phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-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 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 5 articles about phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-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: 100.0%

phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1283073-38-0) + p-toluenesulfonyl chloride (98-59-9) → phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1283073-40-4)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In acetonitrile; at 20 ℃;

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 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1283073-40-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: sodium methylate / methanol / 1 h / 20 °C

2.2: Amberlyst IR 120 resin

3.1: camphorsulfonic acid / Reflux

4.1: N,N,N,N,-tetramethylethylenediamine / acetonitrile / 20 °C

With N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo102411j

Reference yield:

thiophenol (108-98-5) → phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (1283073-40-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: sodium methylate / methanol / 1 h / 20 °C

2.2: Amberlyst IR 120 resin

3.1: camphorsulfonic acid / Reflux

4.1: N,N,N,N,-tetramethylethylenediamine / acetonitrile / 20 °C

With N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo102411j

upstream raw materials:

phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

p-toluenesulfonyl chloride

thiophenol

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

Downstream raw materials:

C₃₈H₅₄Cl₆N₂O₁₉S