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

Base Information

• Chemical Name: 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 99049-62-4
• Molecular Formula: C₂₉H₂₉Cl₃N₄O₅
• Molecular Weight: 619.932
• Mol file: 99049-62-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 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: 81.0%

(3R,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-ol + trichloroacetonitrile (545-06-2) → 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 4 ℃; for 16h;

DOI:10.1016/j.mencom.2007.01.004

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃, cer(III)-ammonium nitrate / acetonitrile / 20 h / -20 °C

2: aq. sodium nitrite / dioxane / 80 °C

3: 1.) NaH; 2.) NaH / 1.) ethyleneglycol-dimethylether, O deg C, 0.5 h; 2.) 3.5 h

With sodium azide; cerium(III) ammonium nitrate; sodium hydride; sodium nitrite; In 1,4-dioxane; acetonitrile;

Reference yield:

(3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-2-nitrooxy-tetrahydro-pyran → 2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. sodium nitrite / dioxane / 80 °C

2: 1.) NaH; 2.) NaH / 1.) ethyleneglycol-dimethylether, O deg C, 0.5 h; 2.) 3.5 h

With sodium hydride; sodium nitrite; In 1,4-dioxane;

upstream raw materials:

trichloroacetonitrile

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

N-(2-Azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-trichloracetamid

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-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

tert-butyldimethylsilyl 2-azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-2-deoxy-4,6-O-isopropylidene-β-D-galactopyranoside