6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside
• CAS No.: 236115-71-2
• Molecular Formula: C₁₉H₂₂O₇S₂
• Molecular Weight: 426.511
• Mol file: 236115-71-2.mol

Synonyms:6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside

Chemical Property of 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside

There total 2 articles about 6-(4-methylbenzenesulfonate)-phenyl-1-thio-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: 75.0%

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) + p-toluenesulfonyl chloride (98-59-9) → 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside (236115-71-2)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 20h;

DOI:10.1021/ja9910356

Reference yield:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → 6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside (236115-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / sodium methoxide / methanol / 18 h / 20 °C

2: 60 percent / pyridine / 0 - 20 °C

With pyridine; sodium methylate; In methanol;

DOI:10.1039/b505865a

Reference yield: 90.0%

6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside (236115-71-2) → 6-azido-6-deoxy-1-phenylthio-β-D-glucopyranoside (236115-72-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 5h;

DOI:10.1021/ja9910356

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

p-toluenesulfonyl chloride

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

6-azido-6-deoxy-1-phenylthio-β-D-glucopyranoside