(2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane

Base Information

• Chemical Name: (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane
• CAS No.: 141783-42-8
• Molecular Formula: C₁₁H₁₄O₄S
• Molecular Weight: 242.296
• Mol file: 141783-42-8.mol

Synonyms:(2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane

Chemical Property of (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane

There total 6 articles about (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane 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: 67.0%

(E/Z)-2-buten-1-ol (6117-91-5,542-72-3) + p-toluenesulfonyl chloride (98-59-9) → (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane (141783-42-8)

Guidance literature:

(E/Z)-2-buten-1-ol; With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

With tert.-butylhydroperoxide; In dichloromethane; at -20 ℃; for 2h; Inert atmosphere;

p-toluenesulfonyl chloride; With dmap; triethylamine; triphenylphosphine; In dichloromethane; at -20 - -10 ℃; for 36h; Inert atmosphere;

Reference yield: 67.0%

(E)-but-2-enol (504-61-0,542-72-3) + p-toluenesulfonyl chloride (98-59-9) → (2S,3S)-2-(4-methylbenzenesulfonyloxymethyl)-3-methyloxirane (141783-42-8)

Guidance literature:

(E)-but-2-enol; With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

With tert.-butylhydroperoxide; In dichloromethane; at -20 ℃; for 4h; Inert atmosphere; Molecular sieve;

p-toluenesulfonyl chloride; With dmap; triethylamine; phosphorous acid trimethyl ester; In dichloromethane; at -20 - -10 ℃; for 30h; Inert atmosphere; Molecular sieve;

DOI:10.1002/anie.201914620

Reference yield: 58.0%

(2R/3R)/(2S,3S)-2,3-epoxy-butanol (55058-23-6,26097-34-7) + p-toluenesulfonyl chloride (98-59-9) → trans-2-(p-Toluenesulfonyloxymethyl)-3-methyloxirane (19300-58-4,107033-47-6,121157-12-8,141783-42-8)

Guidance literature:

With pyridine; at -10 ℃; for 48h;

DOI:10.1055/s-1988-27731

upstream raw materials:

(2R/3R)/(2S,3S)-2,3-epoxy-butanol

p-toluenesulfonyl chloride

(2S,3S)-2,3-epoxy-1-butanol

(E)-but-2-enol

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3S)-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-methyl-non-4-ynyl ester

Toluene-4-sulfonic acid (2R,3S)-6-(tert-butyl-dimethyl-silanyloxy)-8,8-diethoxy-2-hydroxy-3-methyl-oct-4-ynyl ester

(R/S)-1,2-Butandiol-1-<(4-methylbenzol)sulfonat>

(R)-2-hydroxybutyl p-toluenesulfonate