121468-44-8

Basic information

• Product Name: Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester
• Synonyms: Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester
• CAS NO: 121468-44-8
• Molecular Weight: 324.441
• Mol File: 121468-44-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester(121468-44-8)
• EPA Substance Registry System: Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester(121468-44-8)

Safety Data

• Hazardous Substances Data: 121468-44-8(Hazardous Substances Data)

Upstream product

• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-24-1 Geraniol 

Downstream Products

• 126-91-0 linalool 
• 126-90-9 (S)-(+)-linalool 

Relevant articles and documents

Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination

The total synthesis of cytotoxic meroditerpenoid naphthoquinone derivative chabrolonaphthoquinone B (1) in an enantiospecific manner is divulged using a chiral pool approach. The key step of our synthetic route is a modified Julia olefination between a sulfone-bearing aliphatic fragment and a Diels-Alder-derived aromatic aldehyde, leading to the stereoselective construction of the E-trisubstituted double bond.

Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol

The first total syntheses of (+)-thyrsiferol (1), (+)-thyrsiferyl 23-acetate (3), and (+)-venustatriol (5) have been accomplished in a stereoselective manner.An effective synthetic scheme to construct the BC ring system, which adopts a chair/twist-boat conformation, was first developed by means of a model study.This method involves stereoselective formation of the strained C ring by intramolecular attack of the C7-hydroxyl group at the C3-postion of the 2,3-epoxy alcohol, employing titanium tetraisopropoxide as an acidic activator.Based on the information accumulated in the model study and retrosynthetic considerations, the total syntheses of 1,3, and 5 were performed in the sequence of (1) construction of the BC ring system equipped with a C1-C6 carbon unit, (2) elongation of the C17-C24 carbon chain, (3) formation of a D ring through the stereoselective epoxidation of the 4-en-1-ol system and successive cyclization, and (4) construction of the A ring by bromonium ion induced cyclization of the 4-en-1-ol system.