74004-31-2

Usage

InChI:InChI=1/C17H26O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h3,5-8,10-11,14,16,18H,2,4,9,12-13,15H2,1H3,(H,19,20)/b7-5+,8-6+,10-3+,14-11+

Upstream product

• 14273-92-8 methyl 5-hydroxypentanoate 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 127309-14-2 (S,Z)-1-((2R,3R)-3-(trimethylsilyl)oxiran-2-yl)hex-3-en-1-ol 
• 127268-92-2 (R,Z)-1-((2R,3R)-3-(trimethylsilyl)oxiran-2-yl)hex-3-en-1-ol 
• 1070971-82-2 (3S,1E,5Z)-1-iodoocta-1,5-diene-3-ol 
• 76047-91-1 methyl (5Z)-non-5-en-8-ynoate 
• 127309-13-1 (R,1E,5Z)-1-(trimethylsilyl)octa-1,5-dien-3-ol 
• 127268-92-2 (S,Z)-1-((2S,3S)-3-(trimethylsilyl)oxiran-2-yl)hex-3-en-1-ol 
• 6026-86-4 methyl 4-formylbutanoate 
• 127268-91-1 (1E,5Z)-1-(trimethylsilyl)octa-1,5-dien-3-ol 

Relevant academic research and scientific papers

Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives

Natural 12-hydroxyheptadecatrienoic acid (12-HHT) with an S configuration was synthesised by a Suzuki-Miyaura coupling of C10-C17 iodo alcohol with C1-C9 vinylborane. The iodo alcohol was synthesised by utilising Sharpless asymmetric epoxidation of the corresponding trimethylsilyl alcohol. The method yielded more than 100 mg of 12-HHT. Similarly, syntheses of 5,6-dihydro- and 14,15-dehydro derivatives of 12-HHT, known as HHD and HHTE, respectively, were completed in a stereoselective manner.