phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside
• CAS No.: 1301693-36-6
• Molecular Formula: C₃₅H₃₇N₃O₅SSi
• Molecular Weight: 639.847
• Mol file: 1301693-36-6.mol

Synonyms:phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

There total 11 articles about phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-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: 99.0%

phenyl 2-deoxy-2-azido-3-O-benzoylthio-β-D-glucopyranoside + tert-butylchlorodiphenylsilane (58479-61-1) → phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside (1301693-36-6)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃;

DOI:10.1021/acs.orglett.6b02241

Reference yield:

benzoyl chloride (98-88-4) → phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside (1301693-36-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dimethyltin dichloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 0.08 h / Inert atmosphere

1.2: 2.5 h / 20 °C / Inert atmosphere

2.1: camphor-10-sulfonic acid / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

4.1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

5.1: water; acetic acid / 1.5 h / 85 °C / Inert atmosphere

6.1: 1H-imidazole / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium azide; camphor-10-sulfonic acid; water; dimethyltin dichloride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo200342v

Reference yield:

thiophenol (108-98-5) → phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside (1301693-36-6)

Guidance literature:

Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate / dichloromethane / 48 h / 0 °C

2: sodium methylate / methanol

3: camphor-10-sulfonic acid / acetonitrile

4: diethyl ether; Petroleum ether

5: dmap; triethylamine / dichloromethane / 20 °C

6: toluene-4-sulfonic acid / dichloromethane; methanol / 20 °C

7: 1H-imidazole / acetonitrile / 20 °C

With 1H-imidazole; dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; triethylamine; In methanol; diethyl ether; dichloromethane; acetonitrile; Petroleum ether;

DOI:10.1021/acs.orglett.6b02241

upstream raw materials:

phenyl 3-O-benzoyl-1-thio-β-D-mannopyranoside

tert-butylchlorodiphenylsilane

phenyl-1-thio-β-D-mannopyranoside

benzoyl chloride

Downstream raw materials:

phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside

phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-t-butyldiphenylsilyl-4-O-t-butyloxycarbonyl-1-thio-β-D-galactopyranoside

phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-4-O-tert-butyloxycarbonyl-1-thio-β-D-glucopyranoside