allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 97562-22-6
• Molecular Formula: C₄₀H₄₇Cl₃N₂O₁₆
• Molecular Weight: 918.176
• Mol file: 97562-22-6.mol

Synonyms:allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 2 articles about allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside 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: 45.0%

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) + allyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (92949-52-5) → allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (97562-22-6)

Guidance literature:

With mercury(II) cyanide; In chloroform; for 0.666667h; Heating;

DOI:10.1246/bcsj.60.2205

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9) → allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (97562-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dry HBr / CH₂Cl₂ / 18 h / Ambient temperature; in a sealed flask

2: 45 percent / mercury(II) cyanide / CHCl₃ / 0.67 h / Heating

With hydrogen bromide; mercury(II) cyanide; In dichloromethane; chloroform;

DOI:10.1246/bcsj.60.2205

Reference yield:

allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside (97562-22-6) → Benzoic acid (2R,3R,4R,5S,6R)-3-acetylamino-2-allyloxy-5-benzyloxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester

Guidance literature:

With Zn,AcOH; zinc; at 45 ℃;

DOI:10.1016/S0040-4039(00)61962-7

upstream raw materials:

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

allyl 2-acetamido-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

Downstream raw materials:

allyl 2-acetamido-6-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside