138253-43-7

Basic information

• Product Name: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide
• Synonyms: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide
• CAS NO: 138253-43-7
• Molecular Weight: 366.478
• Mol File: 138253-43-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide(138253-43-7)
• EPA Substance Registry System: (6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide(138253-43-7)

Safety Data

• Hazardous Substances Data: 138253-43-7(Hazardous Substances Data)

Upstream product

• 138253-40-4 Methanesulfonic acid (R)-(1R,6R,9S)-1-(11,12-dioxa-tricyclo[7.2.1.0^1,6]dodec-6-yl)-ethyl ester 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 138253-36-8 (-)-(1R,6S,9S)-6-ethoxycarbonyl-11,12-dioxatricyclo<7.2.1.0^1,6>dodecane 
• 138253-39-1 (-)-(1R,6R,9S)-6-<(1'R)-1'-hydroxy>ethyl-11,12-dioxatricyclo<7.2.1.0^1,6>dodecane 
• 138253-37-9 1-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 138253-38-0 (-)-(1R,6R,9S)-6-acetyl-11,12-dioxatricyclo<7.2.1.0^1,6>dodecane 
• 67987-67-1 (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane 
• 138253-42-6 (6Z,9S)-6-ethylidene-9-hydroxymethyl-9-nonanolide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 61448-27-9 (R)-(-)-phoracantholide I 

Relevant articles and documents

Synthesis of (R)-(-)-phoracantholide I based on stereocontrolled cleavage of internal acetal

Oxidation of (S)-2-butenyl-2-ethoxycarbonylcyclohexanone (6) with MCPBA afforded directly two chiral internal acetals, 1S,6S,9R-(8) and 1R,6S,9S-(9), instead of the epoxide. By treatment with BF3 etherate, the tertiary alcohol (12) obtained from 9 yielded an unexpected product (14) via the retro-aldol reaction and reconstruction of the internal acetal, and the expected fragmentation product (3) was not obtained. The mesylate of secondary alcohol (15b) prepared from 9 underwent silica-gel catalyzed, facile ring cleavage in a stereocontrolled fashion to afford the ring-enlarged 9-nonanolide derivatives (18). This methodology was applied for the synthesis of (R)-(-)-phoracantholide I. Examination using the Dreiding stereomodel provides a rationalized explanation for the stereocontrolled cleavage.