p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside

Base Information

• Chemical Name: p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside
• CAS No.: 1426447-50-8
• Molecular Formula: C₃₂H₃₈O₆SSi
• Molecular Weight: 578.802
• Mol file: 1426447-50-8.mol

Synonyms:p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside

Chemical Property of p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside

There total 16 articles about p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside 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: 90.0%

4-methylphenyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside (1415218-09-5) + t-butyldimethylsiyl triflate (69739-34-0) → p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside (1426447-50-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -40 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201205601

Reference yield:

1,2,3,4-tetra-O-acetyl-D-xylopyranose (62446-93-9) → p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside (1426447-50-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 20 h / 20 °C / Inert atmosphere

2.1: sodium methylate / dichloromethane; methanol / 20 °C / pH 12 / Inert atmosphere

2.2: pH 7 / Inert atmosphere

3.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / dichloromethane; methanol / 20 °C / Inert atmosphere

6.1: dmap / dichloromethane / Inert atmosphere; Reflux

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine / dichloromethane / -40 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201205601

Reference yield:

p-methylphenyl 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside (61025-08-9) → p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside (1426447-50-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium methylate / dichloromethane; methanol / 20 °C / pH 12 / Inert atmosphere

1.2: pH 7 / Inert atmosphere

2.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / dichloromethane; methanol / 20 °C / Inert atmosphere

5.1: dmap / dichloromethane / Inert atmosphere; Reflux

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / -40 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; sodium methylate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201205601

upstream raw materials:

benzoyl chloride

4-methylphenyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside

t-butyldimethylsiyl triflate

D-Xylose

Downstream raw materials:

N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-β-D-xylopyranosyl)-L-serine benzyl ester