8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside

Base Information

• Chemical Name: 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS No.: 81414-85-9
• Molecular Formula: C₂₆H₃₈O₉
• Molecular Weight: 494.582
• Mol file: 81414-85-9.mol

Synonyms:8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside

Chemical Property of 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside

There total 3 articles about 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside 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:

Benzoic acid (3aS,4R,6R,7R,7aS)-6-(8-methoxycarbonyl-octyloxy)-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (81414-86-0) → 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside (81414-85-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 10343 Torr; Yield given;

DOI:10.1139/v82-012

Reference yield:

8-methoxycarbonyloctyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (68733-32-4) → 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside (81414-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 80percent aq. acetic acid 2.) p-toluenesulphonic acid

2: hydrogen / 5percent palldium-on-charcoal / ethanol / 10343 Torr

With hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In ethanol;

DOI:10.1139/v82-012

Reference yield:

8-methoxycarbonyloctyl 4,6-O-benzylidene-β-D-galactopyranoside (65567-22-8) → 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside (81414-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) chloroacetyl chloride, pyridine; 2.) benzoylating agent / 1.) dichloroethane, dichloromethane, -78 deg C

2: 1.) 80percent aq. acetic acid 2.) p-toluenesulphonic acid

3: hydrogen / 5percent palldium-on-charcoal / ethanol / 10343 Torr

With pyridine; benzoylating agent; hydrogen; toluene-4-sulfonic acid; acetic acid; chloroacetyl chloride; palladium on activated charcoal; In ethanol;

DOI:10.1139/v82-012

upstream raw materials:

Benzoic acid (3aS,4R,6R,7R,7aS)-6-(8-methoxycarbonyl-octyloxy)-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

8-methoxycarbonyloctyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

8-methoxycarbonyloctyl 4,6-O-benzylidene-β-D-galactopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 6-O-<3,6-di-O-acetyl-4-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl>-2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside

8-methoxycarbonyloctyl 6-O-<4,6-di-O-acetyl-3-O-(tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl>-2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside