8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS No.: 1323024-77-6
• Molecular Formula: C₃₅H₄₄BrCl₃N₄O₁₇
• Molecular Weight: 979.014
• Mol file: 1323024-77-6.mol

Synonyms:8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property of 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

There total 4 articles about 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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: 77.0%

8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1323024-76-5) → 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1323024-77-6)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; 1,1,2,2-tetrachloroethane; at 100 ℃; for 2h; regioselective reaction;

DOI:10.1016/j.carres.2011.02.011

Reference yield:

ethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside (399035-92-8) → 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1323024-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 1 h / -10 °C / Inert atmosphere; Molecular sieve

2: N-Bromosuccinimide; barium carbonate / tetrachloromethane; 1,1,2,2-tetrachloroethane / 2 h / 100 °C

With N-Bromosuccinimide; N-iodo-succinimide; silver trifluoromethanesulfonate; barium carbonate; In tetrachloromethane; dichloromethane; 1,1,2,2-tetrachloroethane;

DOI:10.1016/j.carres.2011.02.011

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (1323024-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,4,6-trimethyl-pyridine / dichloromethane / 0.5 h / Inert atmosphere; Molecular sieve

1.2: 4 h / -30 - 20 °C / Inert atmosphere; Molecular sieve

2.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 1 h / -10 °C / Inert atmosphere; Molecular sieve

3.1: N-Bromosuccinimide; barium carbonate / tetrachloromethane; 1,1,2,2-tetrachloroethane / 2 h / 100 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; N-iodo-succinimide; silver trifluoromethanesulfonate; barium carbonate; In tetrachloromethane; dichloromethane; 1,1,2,2-tetrachloroethane;

DOI:10.1016/j.carres.2011.02.011

upstream raw materials:

8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-deoxy-2-N-trichloroacetamido-1-thio-β-D-glucopyranoside

ethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosyluronate)-β-D-glucopyranoside