306769-38-0

Basic information

• Product Name: (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene
• Synonyms: (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene
• CAS NO: 306769-38-0
• Molecular Weight: 594.951
• Mol File: 306769-38-0.mol

Chemical Properties

• CAS DataBase Reference: (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene(306769-38-0)
• EPA Substance Registry System: (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene(306769-38-0)

Safety Data

• Hazardous Substances Data: 306769-38-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 306769-35-7 (3S,4S,11R,16R)-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-en-17-ol 
• 171625-51-7 3β-(Triisopropylsiloxy)-11α-hydroxy-3,4,8-epi-17,18-dinoraphidicol-6-en-16-one 
• 171756-30-2 (4E,6E,12E)-(8S,9S)-8,12-dimethyl-13-hydroxymethyl-9-(triisopropylsilyloxy)cyclopentadeca-4,6,12-trien-1-one 
• 171756-31-3 (4E,6E,12E)-(8S,9S)-8,12-dimethyl-13-formyl-9-(triisopropylsilyloxy)cyclopentadeca-4,6,12-trien-1-one 
• 228252-17-3 (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal 
• 228252-15-1 (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-N-methoxy-7-methoxymethyl-N,2,6-trimethyl-3-(triisopropylsilyl)oxy-6-octenamide 
• 263155-35-7 (2E,8E)-(6S,7S)-3,7-dimethyl-9-iodo-2-methoxymethyl-6-(triisopropylsilyloxy)nona-2,8-dien-1-ol 
• 263155-40-4 (4E,6E,12E)-(8S,9S)-8,12-dimethyl-13-methoxymethyl-9-(triisopropylsilyloxy)cyclopentadeca-4,6,12-trien-1-one 
• 263155-36-8 (1E,7Z)-(3S,4S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-iodo-8-methoxymethyl-3,7-dimethyl-4-triisopropylsilanyloxy-nona-1,7-diene 
• 263155-41-5 Acetic acid (1E,7E,9E)-(5S,6S)-2,6-dimethyl-13-oxo-5-triisopropylsilanyloxy-cyclopentadeca-1,7,9-trienylmethyl ester 
• 263155-42-6 (3S,4S,11R)-8-epi-17-methoxy-19-nor-3-(triisopropylsilyloxy)aphidicola-6,16-dien-11-ol 
• 263155-39-1 (4E,6E,12E)-(8S,9S,15RS)-15-(tert-butoxy)carbonyl-8,12-dimethyl-13-methoxymethyl-9-(triisopropylsilyloxy)cyclopentadeca-4,6,12-trien-1-one 
• 263155-38-0 (6E,8E,14Z)-(10S,11S)-15-Chloromethyl-16-methoxy-10,14-dimethyl-3-oxo-11-triisopropylsilanyloxy-hexadeca-6,8,14-trienoic acid tert-butyl ester 

Downstream Products

• 306769-39-1 (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-noraphidicol-6-en-3-ol 

Relevant articles and documents

New approach to aphidicolin and total asymmetric synthesis of unnatural (11R)-(-)-8-epi-11-hydroxyaphidicolin by tandem transannular diels-alder/aldol reactions

The 8-epiaphidicolane skeleton (3) was formed in one key reaction by highly diastereoselective tandem transannular Diels-Alder (TADA)-aldol reactions from the trans-trans-cis trienic macrocycle (4). The unnatural derivative (11R)-(-)-8-epi-11-hydroxyaphidicolin (2) was thus constructed, and an original solution to the C16 functionalization problem of many aphidicolin (1) syntheses is presented.