(4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide

Base Information

• Chemical Name: (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide
• CAS No.: 1206227-46-4
• Molecular Formula: C₁₀H₁₉NO₅S
• Molecular Weight: 265.331
• Hs Code.: 2934100090
• Mol file: 1206227-46-4.mol

Synonyms:(4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide

Chemical Property of (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

(4S)-2,2-Dioxido-4-isopropyl -1,2,3-oxathiazolidine, N-Boc protected? ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide

There total 5 articles about (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide 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: 85.0%

(S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol (79069-14-0) → (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide (1206227-46-4)

Guidance literature:

(S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol; With triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

With sulfuryl dichloride; In dichloromethane; at -20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1080/10426507.2016.1274992

Reference yield:

C10H19NO4S → (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide (1206227-46-4)

Guidance literature:

With sodium periodate; ruthenium(III) chloride trihydrate; In water; acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo902302c

Reference yield:

(S)-valinol (2026-48-4,473-75-6) → (4S)-4-iso-propyl-1,2,3-oxathiazolidine-3-carboxylic acid 1,1-dimethylethyl ester 2,2-dioxide (1206227-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / tetrahydrofuran; water / Cooling with ice

2: thionyl chloride; pyridine / acetonitrile / 3 h / -40 - 20 °C / Inert atmosphere

3: rhodium(III) chloride hydrate; sodium periodate / water; acetonitrile / 1 h / 0 - 20 °C

With pyridine; sodium periodate; thionyl chloride; rhodium(III) chloride hydrate; sodium carbonate; In tetrahydrofuran; water; acetonitrile;

DOI:10.1002/adsc.201500110

upstream raw materials:

(S)-valinol

di-tert-butyl dicarbonate

(S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol

L-valine

Downstream raw materials:

(1S)-[1-[(diphenylphosphino)methyl]-2-methylpropyl]carbamic acid 1,1-dimethylethyl ester

(2S)-1-(diphenylphosphino)-3-methylbutan-2-amine

Refernces

• 1、 K'tir, Hacène,Aouf, Zineb,Souk, Tan Otea,Zerrouki, Rachida,Berredjem, Malika,Aouf, Nour-Eddine. "A new family of 1,2,3-oxathiazolidine-2,2-dioxide phosphonate derivatives: Synthesis, characterization and anticancer evaluation". . p. 555 - 559. Retrieved 2017/05/01.
• 2、 Guo, Rongwei,Lu, Shuiming,Chen, Xuanhua,Tsang, Chi-Wing,Jia, Wenli,Sui-Seng, Christine,Amoroso, Dino,Abdur-Rashid, Kamaluddin. "Synthesis of chiral aminophosphines from chiral aminoalcohols via cyclic sulfamidates". supporting information; experimental part. p. 937 - 940. Retrieved 2010/05/02.