O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat

Base Information

• Chemical Name: O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat
• CAS No.: 99049-71-5
• Molecular Formula: C₃₈H₄₂Cl₃N₇O₉
• Molecular Weight: 847.152
• Mol file: 99049-71-5.mol

Synonyms:

Chemical Property of O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat

There total 12 articles about O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat 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: 62.0%

2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-D-glucopyranose + trichloroacetonitrile (545-06-2) → O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosyl>-trichloracetimidat + O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat (99049-71-5)

Guidance literature:

With sodium hydride; for 2h; Yields of byproduct given; Ambient temperature;

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat (99049-71-5)

Guidance literature:

Multi-step reaction with 6 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

4: 92 percent / 0.25 M Et₂O-BF₃, molecular sieve / CH₂Cl₂ / 3 h / -20 °C

5: 68 percent / AcOH, Bu₄NF / tetrahydrofuran / 50 h / Ambient temperature

6: 62 percent / NaH / 2 h / Ambient temperature

With sodium azide; molecular sieve; cerium(III) ammonium nitrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetonitrile;

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-4,6-O-isopropyliden-β-D-glucopyranosid (99049-68-0) → O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat (99049-71-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 0.25 M Et₂O-BF₃, molecular sieve / CH₂Cl₂ / 3 h / -20 °C

2: 68 percent / AcOH, Bu₄NF / tetrahydrofuran / 50 h / Ambient temperature

3: 62 percent / NaH / 2 h / Ambient temperature

With molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane;

upstream raw materials:

trichloroacetonitrile

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

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:

tert-Butyldimethylsilyl-2-azido-3-O-<2-azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-4,6-O-isopropyliden-2-desoxy-β-D-glucopyranosyl>-4,6-O-isopropyliden-2-desoxy-β-D-glucopyranosid