199727-75-8

Basic information

• Product Name: Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester
• Synonyms: Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester
• CAS NO: 199727-75-8
• Molecular Weight: 350.436
• Mol File: 199727-75-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester(199727-75-8)
• EPA Substance Registry System: Toluene-4-sulfonic acid (3S,3aR,7aR)-4,4,7a-trimethyl-2-oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-yl ester(199727-75-8)

Safety Data

• Hazardous Substances Data: 199727-75-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 199727-74-7 (3S,3aR,7aR)-3-Hydroxy-4,4,7a-trimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 199727-73-6 (1R,3S,4S)-5,8,8-Trimethyl-2-oxa-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid ethyl ester 
• 41169-33-9 3,5,5-trimethylcyclohexa-1,3-diene 

Downstream Products

• 17063-17-1 dihydroactinidiolide 

Relevant articles and documents

Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology

The total synthesis of the naturally occurring bicyclic lactones (R)-dihydroactinidiolide and (R)-actinidiolide is presented. The key step in the syntheses is the copper(II)-bisoxazoline-catalyzed hetero-Diels-Alder reaction of a cyclic diene with ethyl glyoxylate giving the hetero-Diels-Alder product in high yield and with very high regio-, diastereo-, and enantioselectivity. The total syntheses proceed via an intermediate, which also has the potential for a series of other natural products. The structure of the key intermediate is confirmed by X-ray analysis.