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

Base Information

• Chemical Name: 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
• CAS No.: 81414-86-0
• Molecular Formula: C₄₅H₅₂O₉
• Molecular Weight: 736.902
• Mol file: 81414-86-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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:

8-methoxycarbonyloctyl 4,6-O-benzylidene-β-D-galactopyranoside (65567-22-8) → 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)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; benzoylating agent; toluene-4-sulfonic acid; acetic acid; chloroacetyl chloride;

DOI:10.1139/v82-012

Reference yield:

trityl chloride (76-83-5) + 8-methoxycarbonyloctyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside (68733-32-4) + 2,2-dimethoxy-propane (77-76-9) → 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)

Guidance literature:

With toluene-4-sulfonic acid; acetic acid; Multistep reaction;

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 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

upstream raw materials:

trityl chloride

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

2,2-dimethoxy-propane

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

Downstream raw materials:

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

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