6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 1392400-66-6
• Molecular Formula: C₅₃H₆₉Cl₅N₂O₂₀
• Molecular Weight: 1231.4
• Mol file: 1392400-66-6.mol

Synonyms:6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 5 articles about 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-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: 100.0%

6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside (1392400-65-5) + chloroacetyl chloride (79-04-9) → 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside (1392400-66-6)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2012.04.020

Reference yield:

6-chlorohexyl 2-acetamido-4-O-(2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-6-O-benzyl-3-O-chloroacetyl-2-deoxy-β-D-glucopyranoside → 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside (1392400-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

2: pyridine; thiourea / ethanol / 19 h / 70 °C

3: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With pyridine; trimethylsilyl trifluoromethanesulfonate; thiourea; In ethanol; dichloromethane;

DOI:10.1021/acs.joc.5b01190

Reference yield:

2,4-di-O-acetyl-3-O-(chloroacetyl)-6-O-pivaloyl-α-D-galactopyranosyl trichloroacetimidate → 6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside (1392400-66-6)

Guidance literature:

Multi-step reaction with 5 steps

1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 40 °C / Inert atmosphere

2: pyridine; thiourea / ethanol / 4 h / 55 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

4: pyridine; thiourea / ethanol / 19 h / 70 °C

5: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With pyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; thiourea; In ethanol; dichloromethane;

DOI:10.1021/acs.joc.5b01190

upstream raw materials:

6-chlorohexyl 2-acetamido-4-O-[2,4-di-O-acetyl-6-O-pivaloyl-3-O-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-galactopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranoside

chloroacetyl chloride

6-chlorohexyl 2-acetamido-6-O-benzyl-3-O-chloroacetyl-2-deoxy-β-D-glucopyranoside