156159-40-9

Upstream product

• 156159-39-6 (2R,3E)-1-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxy-3-octadecene 
• 1352742-30-3 (2R)-ethyl 2-hydroxyoctadec-3-ynoate 
• 629-74-3 hexadec-1-yne 
• 22566-56-9 ethyl 2-oxooctadec-3-ynoate 
• 131606-87-6 (2R,3E)-octadec-3-ene-1,2-diol 
• 156159-37-4 (2R,3E)-1-tert-butyldimethylsilyloxy-3-octadecen-2-ol 
• 156159-34-1 (2S,3S)-1-tert-butyldimethylsilyloxy-2,3-epoxyoctadecane 
• 136598-22-6 (2S,3S)-2,3-epoxyoctadecan-1-ol 

Downstream Products

• 156199-15-4 (2R,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane 
• 1352742-33-6 (2R,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-2-aminooctadecane-1,3-diol 
• 1352742-39-2 (2R,3R,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane 
• 1352742-40-5 (2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-isopropylidenedioxy-2-aminooctadecane 
• 1352742-41-6 (2R,3R,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-2-aminooctadecane-1,3-diol 
• 1352742-42-7 (2S,3S,2'R,3'E)-N-(2'-tert-butyldiphenylsilyloxy-3'-octadecenoyl)-2-aminooctadecane-1,3-diol 
• 156257-69-1 (2S,2'R,3R,3'E)-N-(2'-t-butyldiphenylsilyloxy-3'-octadecenoyl)-<2-amino-1,3-dihydroxyoctadecane> 
• 156159-44-3 (2S,2'R,3R,3'E)-N-(2'-t-butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-O-isopropyliden-<2-amino-1,3-dihydroxyoctadecane> 
• 118106-53-9 (2S,3R,2'R,3'E)-2-N-(2'-hydroxy-3'-octadecenoyl)-[2-amino-octadecan-1,3-diol] 
• 156159-42-1 (2R,3E)-2-(tert-Butyldiphenylsilyloxy)-3-octadecanoic acid 

Relevant academic research and scientific papers

Total synthesis of symbioramide: A flexible approach for the efficient preparation of structural isomers

A concise, enantioselective total synthesis of symbioramide, starting from simple achiral compounds and racemic α-amino-β-keto ester derivatives is reported. This highly flexible strategy allowed the efficient preparation of seven structural isomers of the natural product as well. The synthesis relies on a convergent route that involves the efficient stereoselective reduction of a α-keto-β-yne ester, and the dynamic kinetic resolution of an α-amino-β-keto ester through ruthenium-mediated asymmetric hydrogenation. Copyright

Synthesis of Sphingosine Relatives, XIV. A New Synthesis of Symbioramide, a Ca(++)-ATPase Activator from Symbiodinium sp.

Symbioramide was synthesized from D-erythro-dihydrosphingosine (19) and (R,E)-2'-tert-butyldimethylsilyloxy-3'-octadecenoic acid (14), which was prepared from (E)-2-octadecen-1-ol (4) by employing the Sharpless asymmetric epoxidation.The (2S,2'S,3R,3'E)-isomer 28 of 1 was also synthesized to further confirm the structure of 1. - Key Words: Ca(++)-ATPase activator / Ceramides / Marine natural products / Sphingosines / Symbioramide