Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester
• CAS No.: 121401-06-7
• Molecular Formula: C₁₇H₂₄O₄S
• Molecular Weight: 324.441
• Mol file: 121401-06-7.mol

Synonyms:Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester

Chemical Property of Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester

There total 2 articles about Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl 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: 94.0%

(2S,3S)-2,3-epoxygeraniol (82188-73-6) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester (121401-06-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -10 ℃;

DOI:10.1021/jo00055a029

Reference yield:

Geraniol (106-24-1) → Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester (121401-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / (+)-DIPT,m Ti(OiPr)4, t-BuOOH, molecular sieves 4 Angstroem / CH₂Cl₂ / -34 °C

2: 94 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / -10 °C

With tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; 4 A molecular sieve; triethylamine; In dichloromethane;

DOI:10.1021/jo00055a029

Reference yield: 97.0%

Toluene-4-sulfonic acid <3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl>methyl ester (121401-06-7) → linalool (126-91-0) + (S)-(+)-linalool (126-90-9)

Guidance literature:

With sodium hydroxide; tellurium; rongalite; In tetrahydrofuran; water; at 50 - 55 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)77252-2

upstream raw materials:

(2S,3S)-2,3-epoxygeraniol

p-toluenesulfonyl chloride

Geraniol

Downstream raw materials:

(S)-(+)-linalool

linalool

Toluene-4-sulfonic acid (R)-3-hydroxy-3,7-dimethyl-oct-6-enyl ester

(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

Refernces

• 1、 Smart, Mary A.,McDonald, Frank E.. "Synthesis of 15,28-dideoxy-15,28-didehydrothyrsenol". . p. 535 - 553. Retrieved 2013/08/15.
• 2、 Taber, Douglas F.,Bhamidipati, Rama S.,Thomas, Mitchell L.. "Cascade Cyclization: Synthesis of (+)-Tuberine". . p. 3442 - 3444. Retrieved 2007/10/02.