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

Base Information

• Chemical Name: 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
• CAS No.: 81415-09-0
• Molecular Formula: C₅₈H₇₃NO₂₆
• Molecular Weight: 1200.21
• Mol file: 81415-09-0.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 64.0%

3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α/β-D-glucopyranosyl chloride (81445-63-8) + 8-methoxycarbonyloctyl 2-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranoside (81414-85-9) → 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 (81415-09-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In nitromethane; 1.) -15 deg C, 1 h; 2.) r.t, 2 h;

DOI:10.1139/v82-012

Reference yield:

8-methoxycarbonyloctyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (68733-32-4) → 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 (81415-09-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 64 percent / silver trifluoromethylsulfonate, sym-collidine / nitromethane / 1.) -15 deg C, 1 h; 2.) r.t, 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In nitromethane; ethanol;

DOI:10.1139/v82-012

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 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 (81415-09-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 64 percent / silver trifluoromethylsulfonate, sym-collidine / nitromethane / 1.) -15 deg C, 1 h; 2.) r.t, 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In nitromethane; ethanol;

DOI:10.1139/v82-012

upstream raw materials:

3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α/β-D-glucopyranosyl chloride

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

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

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