1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose

Base Information

• Chemical Name: 1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose
• CAS No.: 403604-98-8
• Molecular Formula: C₁₉H₂₄O₇
• Molecular Weight: 364.395
• Mol file: 403604-98-8.mol

Synonyms:1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose

Chemical Property of 1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose

There total 4 articles about 1-O-Benzoyl-2,3:5,6-di-O-isopropylidene-D-talofuranose 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:

2,3,5,6-di-O-isopropylidene-L-gulono-1,4-lactone (23262-80-8) → Benzoic acid (3aS,6S,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester (403604-98-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / toluene

2: pyridine

With diisobutylaluminium hydride; In pyridine; toluene;

DOI:10.1016/S0040-4039(03)00552-5

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone (7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6) → Benzoic acid (3aS,6S,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester (403604-98-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethyl acetate / 4 h / 20 °C

2.1: MsCl; Et₃N; dimethylaminopyridine / ethyl acetate / 5 h / 20 °C

2.2: water / ethyl acetate / 20 °C

3.1: DIBAL-H / toluene

4.1: pyridine

With dmap; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; In pyridine; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(03)00552-5

Reference yield:

{(4S,5S)-5-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-piperidin-1-yl-methanone → Benzoic acid (3aS,6S,6aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester (403604-98-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MsCl; Et₃N; dimethylaminopyridine / ethyl acetate / 5 h / 20 °C

1.2: water / ethyl acetate / 20 °C

2.1: DIBAL-H / toluene

3.1: pyridine

With dmap; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; In pyridine; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(03)00552-5

upstream raw materials:

benzoyl chloride

2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone

2,3,5,6-di-O-isopropylidene-L-gulono-1,4-lactone

Downstream raw materials:

Benzoic acid (3aS,6S,6aS)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

2,3-O-isopropylidene-L-ribofuranose

Refernces