tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside
• CAS No.: 1384556-68-6
• Molecular Formula: C₂₉H₃₅N₃O₇SSi
• Molecular Weight: 597.764
• Mol file: 1384556-68-6.mol

Synonyms:tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside

Chemical Property of tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside

There total 4 articles about tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-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: 83.0%

tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside (501088-46-6) + p-toluenesulfonyl chloride (98-59-9) → tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside (1384556-68-6)

Guidance literature:

In pyridine; at 0 ℃; for 2h; regioselective reaction;

DOI:10.1016/j.carres.2012.02.015

Reference yield:

2-azido-2-deoxy-D-glucose → tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside (1384556-68-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 20 °C

2: piperidine / tetrahydrofuran / 2.5 h

3: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C

4: sodium methylate / methanol; dichloromethane

5: pyridine / 2 h / 0 °C

With piperidine; 1H-imidazole; sodium methylate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2012.02.015

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → tert-butyldiphenylsilyl 2-azido-2-deoxy-6-O-tosyl-β-D-glucopyranoside (1384556-68-6)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole-1-sulfonyl azide hydrochloride; copper(II) sulfate; triethylamine / methanol / 1.5 h

2: pyridine / 20 °C

3: piperidine / tetrahydrofuran / 2.5 h

4: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C

5: sodium methylate / methanol; dichloromethane

6: pyridine / 2 h / 0 °C

With piperidine; 1H-imidazole; imidazole-1-sulfonyl azide hydrochloride; sodium methylate; copper(II) sulfate; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2012.02.015

upstream raw materials:

tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside

p-toluenesulfonyl chloride

(+)-D-glucosamine hydrochloride

Downstream raw materials:

4-(N-benzyloxycarbonylamino)-2-azido-3-O-chloroacetyl-2,4,6-trideoxy-β-D-galactopyranose

tert-butyldiphenylsilyl 2-azido-2,6-dideoxy-6-iodo-β-D-glucopyranoside

2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-galactopyranoso)[4,3-d]-1,3-oxazole