(4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester
• CAS No.: 85785-79-1
• Molecular Formula: C₁₈H₂₄O₈S
• Molecular Weight: 400.45
• Mol file: 85785-79-1.mol

Synonyms:(4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Chemical Property of (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

There total 2 articles about (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl 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: 87.0%

diethyl (2S,3S)-tartrate (13811-71-7) + 4-phenylsulfonyl-2-butanone dimethyl acetal (85785-78-0) → (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (85785-79-1)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 80 - 90 ℃; for 20h;

DOI:10.1016/S0040-4039(00)85892-X

Reference yield:

sodium benzenesulfonate (873-55-2) → (4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (85785-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) AcOH, 2.) c. H₂SO₄ / 1.) EtOH, 15 deg C, 20 h, 2.) MeOH, 15 deg C, 3 h

2: 87 percent / p-TsOH / benzene / 20 h / 80 - 90 °C

With sulfuric acid; toluene-4-sulfonic acid; acetic acid; In benzene;

DOI:10.1016/S0040-4039(00)85892-X

Reference yield:

(4S,5S)-2-(2-Benzenesulfonyl-ethyl)-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester (85785-79-1) → [(4R,5R)-2-(2-Benzenesulfonyl-ethyl)-5-hydroxymethyl-2-methyl-[1,3]dioxolan-4-yl]-methanol (85785-80-4)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 5 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(00)85892-X

upstream raw materials:

diethyl (2S,3S)-tartrate

4-phenylsulfonyl-2-butanone dimethyl acetal

sodium benzenesulfonate

Downstream raw materials:

[(4R,5R)-2-(2-Benzenesulfonyl-ethyl)-5-hydroxymethyl-2-methyl-[1,3]dioxolan-4-yl]-methanol

3-phenylsulfonyl-exo-brevicomin

Toluene-4-sulfonic acid (1R,5R,7R)-3-benzenesulfonyl-5-methyl-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethyl ester

C₂₈H₃₂O₁₀S₃