397322-69-9

Basic information

• Product Name: (S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester
• Synonyms: (S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester
• CAS NO: 397322-69-9
• Molecular Weight: 518.769
• Mol File: 397322-69-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester(397322-69-9)
• EPA Substance Registry System: (S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester(397322-69-9)

Safety Data

• Hazardous Substances Data: 397322-69-9(Hazardous Substances Data)

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 397322-64-4 (S)-(-)-4-oxo-1,2,3-trimethyl-2-cyclohexene-1-carboxylic acid 
• 193468-16-5 (2Z)-(+)-ethyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 88159-03-9 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol 
• 127665-77-4 (E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol 
• 88158-68-3 4-(tert-butyldiphenylsilyloxy)-1-butyne 
• 161807-11-0 5-(tert-butyldiphenylsiloxy)-1-trifluoromethanesulfonyloxy-2-pentene 
• 397322-66-6 (S)-(-)-methyl 4-oxo-1,2,3-trimethyl-2-cyclohexene-1-carboxylate 
• 397322-58-6 ethyl (S)-(-)-2-acetyl-2-methyl-5-oxo-heptanoate 
• 397322-61-1 (S)-(-)-ethyl 4-oxo-1,2,3-trimethyl-2-cyclohexene-1-carboxylate 

Downstream Products

• 397322-74-6 (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone 

Relevant articles and documents

Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin

A full account of studies that culminated in the total synthesis of both antipodes and the assignment of its absolute configuration of Saudin, a hypoglycemic natural product. Two approaches are described, the first proceeding though bicyclic lactone intermediates and related second monocyclic esters. The former was obtained via asymmetric Diels-Alder cycloaddition and the latter by an asymmetric annulation protocol. Both approaches employ a Lewis acid promoted Claisen rearrangement, with the successful approach taking advantage of bidentate chelation to control the facial selectivity of the key Claisen rearrangement.

An enantioselective total synthesis of (+)- and (-)-saudin. Determination of the absolute configuration

A short efficient enantioselective synthesis of both (+)- and (-)-saudin, a naturally occurring hypoglycemic diterpene, is described. This synthesis establishes the absolute configuration of natural (-)-saudin for the first time. The key steps include the