2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
• CAS No.: 151767-11-2
• Molecular Formula: C₃₆H₂₈Cl₃NO₁₀
• Molecular Weight: 740.978
• Mol file: 151767-11-2.mol

Synonyms:2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

There total 9 articles about 2,3,4,5-tetra-O-benzoyl-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: 96.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranose (627466-64-2) + trichloroacetonitrile (545-06-2) → 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (151767-11-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1080/10286020.2012.670220

Reference yield:

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (151767-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: AcO(-)N₂H₅(+) / dimethylformamide / 60 °C

2: DBU / CH₂Cl₂ / 2 h

With hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200204544

Reference yield:

2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide (165877-99-6) + trichloroacetonitrile (545-06-2) → 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (151767-11-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h;

DOI:10.1016/j.carres.2013.04.022

upstream raw materials:

2,3,4,6-tetra-O-benzoyl-D-glucopyranose

trichloroacetonitrile

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside

Downstream raw materials:

gitogenin 2α-O-benzyl-3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)

11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

(25R)-3β-O-[2,4-di-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyl]-26-O-benzoyl-β-D-glucopyranosyl-cholest-5-ene-16,22-dione

ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)