1435818-72-6

Basic information

• Product Name: ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate
• Synonyms: ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate
• CAS NO: 1435818-72-6
• Molecular Weight: 511.531
• Mol File: 1435818-72-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate(1435818-72-6)
• EPA Substance Registry System: ethyl (2E,6E)-2-bromo-8-tert-butyldiphenylsilyloxy-6-methylocta-2,6-dien-4-ynoate(1435818-72-6)

Safety Data

• Hazardous Substances Data: 1435818-72-6(Hazardous Substances Data)

Upstream product

• 26631-69-6 ethyl (E)-2,3-dibromopropenoate 
• 206193-25-1 (2E)-1-tert-butyldiphenylsilyloxy-3-methylpent-2-en-4-yne 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 1435818-76-0 C₂₅H₂₇BrO₃Si 
• 1435818-59-9 (5Z,2’E)-3-bromo-5-(4’-tert-butyldiphenylsilyloxy-2’-methylbut-2’-enylidene)-5H-furan-2-one 

Relevant articles and documents

Total synthesis of enantiopure pyrrhoxanthin: Alternative methods for the stereoselective preparation of 4-alkylidenebutenolides

A new stereocontrolled total synthesis of the configurationally labile C37-norcarotenoid pyrrhoxanthin in enantiopure form has been completed. A highly stereoselective Horner-Wadsworth-Emmons (HWE) condensation of a C17-allylphosphonate and a C20-aldehyde was used as the last conjunctive step. Both a Sonogashira reaction to form the C 17-phosphonate and the final HWE condensation proved to be compatible with the sensitive C7-C10 enyne E configuration. Regioselective (5-exo-dig) silver-promoted lactonization reactions of three alternative pent-2-en-4-ynoic acid precursors with increased complexity, including a fully functionalized C20-fragment, were explored for the preparation of the γ-alkylidenebutenolide fragment. This survey extends the existing methodologies for the preparation of oxygen-containing carotenoids (xanthophylls) and streamlines the synthesis of additional members of the C 37-norcarotenoid butenolide family of natural products. Silver catalysis: A stereocontrolled total synthesis of enantiopure pyrrhoxanthin has been described (see scheme), using a Horner-Wadsworth-Emmons (HWE) condensation as the last step, providing the desired xanthophyll as a single diastereomer. Along this strategy, alkylidenebutyrolactones have been obtained regio- and stereoselectively by silver-promoted lactonization of pentenynoic acids of increasing complexity. Copyright