dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate

Base Information

• Chemical Name: dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate
• CAS No.: 288098-97-5
• Molecular Formula: C₂₁H₂₈O₈S
• Molecular Weight: 440.515
• Mol file: 288098-97-5.mol

Synonyms:dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate

Chemical Property of dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate

There total 1 articles about dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate 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: 70.0%

dimethyl 2-formylcyclopropane-1,1-dicarboxylate (55502-70-0,78918-35-1,141316-73-6,41502-70-9) + tert-butyl (R)-p-toluenesulfinylacetate (58059-08-8) → dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate (288098-97-5)

Guidance literature:

tert-butyl (R)-p-toluenesulfinylacetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

dimethyl 2-formylcyclopropane-1,1-dicarboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 4h;

DOI:10.1016/S0957-4166(00)00120-8

Reference yield:

methanesulfonyl chloride (124-63-0) + dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate (288098-97-5) → 2-[2-tert-butoxycarbonyl-1-methanesulfonyloxy-2-(toluene-4-sulfinyl)-ethyl]-cyclopropane-1,1-dicarboxylic acid dimethyl ester (288098-98-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00120-8

Reference yield:

dimethyl (Rs)-2-[1-hydroxy-2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)ethyl]cyclopropane-1,1-dicarbonate (288098-97-5) → dimethyl (Ss)-2-[2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)vinyl]cyclopropane-1,1-dicarbonate (288072-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 1,8-diazabicyclo[5.4.0]undecene-7 / tetrahydrofuran / 28 h / -20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; 1: mesylation / 2: dehydromesylation;

DOI:10.1016/S0957-4166(00)00120-8

upstream raw materials:

dimethyl 2-formylcyclopropane-1,1-dicarboxylate

tert-butyl (R)-p-toluenesulfinylacetate

Downstream raw materials:

2-[2-tert-butoxycarbonyl-1-methanesulfonyloxy-2-(toluene-4-sulfinyl)-ethyl]-cyclopropane-1,1-dicarboxylic acid dimethyl ester

dimethyl (Ss)-2-[2-(tert-butoxycarbonyl)-2-(p-toluenesulfinyl)vinyl]cyclopropane-1,1-dicarbonate