phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside
• CAS No.: 500212-92-0
• Molecular Formula: C₂₈H₃₃N₃O₄SSi
• Molecular Weight: 535.739
• Mol file: 500212-92-0.mol

Synonyms:phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside

Chemical Property of phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside

There total 9 articles about phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside 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: 94.0%

phenyl 2-deoxy-2-azido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-thio-α-D-galactopyranoside → phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside (500212-92-0)

Guidance literature:

With methanol; sodium methylate; for 0.5h;

DOI:10.3762/bjoc.14.258

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) + phenyl-2-azido-2-deoxy-1-thio-α-D-galactopyranoside → phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside (500212-92-0)

Guidance literature:

With pyridine; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1023/A:1020428329743

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside (500212-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / sodium hydride / tetrahydrofuran / -10 - 5 °C

2: MeONa / methanol / 0.33 h

3: 867 mg / 4-dimethylaminopyridine; pyridine / dimethylformamide / 18 h / 20 °C

With pyridine; dmap; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1023/A:1020428329743

upstream raw materials:

tert-butylchlorodiphenylsilane

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

thiophenol

phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α-D-galactopyranoside

Downstream raw materials:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

2-deoxy-2-azido-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-galactopyranose