tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid

Base Information

• Chemical Name: tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid
• CAS No.: 106567-55-9
• Molecular Formula: C₂₀H₃₁N₃O₆Si
• Molecular Weight: 437.568
• Mol file: 106567-55-9.mol

Synonyms:tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid

Chemical Property of tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid

There total 4 articles about tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid 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: 88.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid (106567-55-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

Reference yield: 62.0%

C14H17N3O6 + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid (106567-55-9)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01803

Reference yield:

2-azido-2-deoxy-β-D-glucose (138889-07-3) → tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-β-D-glucopyranosid (106567-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: CSA / N,N-dimethyl-formamide / 8 h / 40 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b01803

upstream raw materials:

p-Anisaldehyde dimethyl acetal

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

2-azido-2-deoxy-β-D-glucose

D-glucosamine hydrochloride

Downstream raw materials:

tert-Butyldimethylsilyl-4,6-O-anisyliden-2-azido-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid