3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

Base Information

• Chemical Name: 3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose
• CAS No.: 180784-01-4
• Molecular Formula: C₂₀H₂₄O₉
• Molecular Weight: 408.405
• Mol file: 180784-01-4.mol

Synonyms:3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

Chemical Property of 3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

There total 1 articles about 3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose 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: 86.0%

(2S,3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxole-2-carboxylic acid methyl ester (121018-05-1) + benzoyl chloride (98-88-4) → 3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose (180784-01-4)

Guidance literature:

In pyridine;

DOI:10.1007/BF00699946

Reference yield: 88.0%

3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose (180784-01-4) → 3-O-benzoyl-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose (180784-04-7)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 0.166667h;

DOI:10.1007/BF00699946

Reference yield:

3-O-benzoyl-5,6-O-isopropylidene-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose (180784-01-4) → 3,6-di-O-benzoyl-5-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-galactofuranose (152876-37-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / 90percent trifluoroacetic acid / CHCl₃ / 0.17 h

2: 73 percent / imidazole / CHCl₃ / 24 h / Heating

3: 89 percent / 2,4,6-collidine / CH₂Cl₂

4: 1.) ammonia, 2.) benzoyl chloride / 1.) CH₃OH, CHCl₃, 20 deg C, 5 h, 2.) pyridine, 18 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; ammonia; benzoyl chloride; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1007/BF00699946

upstream raw materials:

(2S,3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2-methyl-tetrahydro-furo[2,3-d][1,3]dioxole-2-carboxylic acid methyl ester

benzoyl chloride

Downstream raw materials:

3-O-benzoyl-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

3,6-di-O-benzoyl-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-α-D-galactofuranose

3,6-di-O-benzoyl-5-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-galactofuranose

3,6-di-O-benzoyl-1,2-O-<1-(exo-methoxycarbonyl)ethylidene>-5-O-trityl-α-D-galactofuranose