2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
• CAS No.: 120312-08-5
• Molecular Formula: C₁₉H₃₁N₃O₅Si
• Molecular Weight: 409.558
• Mol file: 120312-08-5.mol

Synonyms:2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Chemical Property of 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

There total 10 articles about 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 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: 92.0%

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2) → 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (120312-08-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 8.5h;

DOI:10.1002/chem.200390009

Reference yield: 74.0%

tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (120312-07-4) → 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (120312-08-5)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1021/jo00305a007

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid (99049-68-0) → 2-azido-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (120312-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / NaH / dimethylformamide / 1.5 h / Ambient temperature

2: 148 mg / 60percent CF₃COOH / CH₂Cl₂ / 1 h

With sodium hydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

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

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

Downstream raw materials:

tert-butyldimethylsilyl 2-azido-3-O-benzyl-2-deoxy-6-O-trityl-β-D-glucopyranoside

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)