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

Base Information

• Chemical Name: tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid
• CAS No.: 106707-64-6
• Molecular Formula: C₄₉H₇₂N₆O₁₁Si₂
• Molecular Weight: 977.315
• Mol file: 106707-64-6.mol

Synonyms:

Chemical Property of tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid

There total 9 articles about tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-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: 39.0%

2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4) → N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid (106567-65-1) + tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106707-64-6) + tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-α-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106567-64-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In hexane; dichloromethane; at -15 ℃;

Reference yield: 6.5%

tert-Butyldimethylsilyl-2-azido-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106567-62-8) + 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4) → N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid (106567-65-1) + tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106707-64-6) + tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-α-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106567-64-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In hexane; dichloromethane; at -15 ℃;

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid (99049-68-0) → tert-Butyldimethylsilyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-6-O-(tert-butyldimethylsilyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranosid (106707-64-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DME, room temp.; 2.) 3 h

2: 70 percent / 60percent CF₃COOH / CH₂Cl₂ / 2 h / Ambient temperature

3: 3 g / pyridine / dimethylformamide / 12 h / 0 °C

4: 39 percent / CF₃SO₃Si(CH₃)3 / CH₂Cl₂; hexane / -15 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; sodium hydride; trifluoroacetic acid; In hexane; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

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

2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

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

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

Downstream raw materials:

1,6-Di-O-acetyl-2-azido-4-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose

2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-1,6-di-O-acetyl-2-desoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose