488808-07-7

Upstream product

• 6064-48-8 1-hydroxy-2(E)-pentadecene 

Downstream Products

• 619315-57-0 (1R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadec-3-yn-1-ol 
• 619315-67-2 (S)-1-[(2S,3R,5R)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-phenylselanyl-tetrahydro-furan-2-yl]-tridecan-1-ol 
• 619315-55-8 tert-butyl-(1-dodecyl-prop-2-ynyloxy)-diphenyl-silane 

Relevant academic research and scientific papers

First asymmetric synthesis of 6-hydroxy-4-sphingenine-containing ceramides. Use of chiral propargylic alcohols to prepare a lipid found in human skin

6-Hydroxy-(4E)-sphingenine-containing ceramides were found recently in human skin. We present here the first synthesis of the 6S and 6R diastereoisomers 2 and 3, which represent analogues of (2S,3R)-ceramide (1) having two allylic hydroxyl groups. Chiral propargylic alcohols 8 and 11, which were prepared by asymmetric dihydroxylation of α,β-unsaturated ester 13 and allylic chloride 22, respectively, were employed as precursors of 2 and 3. Nucleophilic addition of lithiated TBS-protected propargylic ethers 25 and 32 to L-serine-derived aldehyde 26, respectively, afforded oxazolidine intermediates 27 and 33. Acid-mediated deprotection of the oxazolidine, followed by N-acylation and Birch reduction, completed the syntheses of 2 and 3.