1422643-50-2

Upstream product

• 629-11-8 1,6-hexanediol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 103202-59-1 6-(tert-butyldimethylsilyl)oxyhexan-1-ol 
• 1422643-21-7 toluene-4-sulfonic acid 7-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-heptyl ester 
• 1422643-19-3 7-(tert-butyl-dimethyl-silanyloxy)-heptane-1,2-diol 
• 946658-92-0 tert-butyl-dimethyl-(5-oxiranyl-pentyloxy)-silane 
• 1422643-30-8 7-(tert-butyl-dimethyl-silanyloxy)-1-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-heptan-2-ol 
• 1422643-31-9 (S)-tert-butyldimethyl((5-(oxiran-2-yl)pentyl)oxy)silane 
• 166194-76-9 tert-butyl-(hept-6-enyloxy)-dimethyl-silane 
• 118794-69-7 6-[(tert-butyldimethylsilyl)oxy]hexanal 

Relevant academic research and scientific papers

Stereoselective total synthesis of both (6R,9R,10S,7E)- and (6S,9R,10S,7E)-epimers of oxylipin (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid

An asymmetric synthesis of both the stereoisomers (2a & 2b) of the structure 2 proposed for (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, an immunostimulant oxylipin from the n-butanol extract of the corms of Dracontium loretense, has been accomplished. The key steps involved are using Jacobsen's hydrolytic kinetic resolution (HKR), Julia-Kocienski olefination, regioselective epoxide ring opening and Wittig olefination. The configuration (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid was established as 2a from comparison of NMR data, HPLC analysis and [α]D values of naturally derived (9R,10S,7E)-6,9,10-trihydroxyoctadec-7-enoic acid, and comparison with the synthetic diastereomers 2a and 2b.