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

Base Information

• Chemical Name: 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
• CAS No.: 106587-97-7
• Molecular Formula: C₄₁H₄₈N₆O₁₃
• Molecular Weight: 832.865
• Mol file: 106587-97-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 53.0%

acetic anhydride (108-24-7) + 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) → 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 (106587-97-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; 1.) 6 h, reflux, 2.) 3 h;

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid (99049-68-0) → 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 (106587-97-7)

Guidance literature:

Multi-step reaction with 5 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

5: 53 percent / 1 M (NBu₄)F / tetrahydrofuran / 1.) 6 h, reflux, 2.) 3 h

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

Reference yield:

2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4) → 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 (106587-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / CF₃SO₃Si(CH₃)3 / CH₂Cl₂; hexane / -15 °C

2: 53 percent / 1 M (NBu₄)F / tetrahydrofuran / 1.) 6 h, reflux, 2.) 3 h

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

acetic anhydride

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

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:

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