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

Base Information

• Chemical Name: tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside
• CAS No.: 501088-46-6
• Molecular Formula: C₂₂H₂₉N₃O₅Si
• Molecular Weight: 443.575
• Mol file: 501088-46-6.mol

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

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

There total 6 articles about tert-butyldiphenylsilyl 2-azido-2-deoxy-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: 100.0%

(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (344403-81-2) → tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside (501088-46-6)

Guidance literature:

With sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.carres.2012.02.015

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) → tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside (501088-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1: piperidine / tetrahydrofuran / 2.5 h

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

3: sodium methylate / methanol; dichloromethane

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

DOI:10.1016/j.carres.2012.02.015

Reference yield:

2-azido-2-deoxy-D-glucose → tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside (501088-46-6)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1016/j.carres.2012.02.015

upstream raw materials:

(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

(+)-D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

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

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