131606-86-5

Upstream product

• 131606-84-3 (S)-3-octadec-3-yne-1,2-diol 
• 131606-82-1 (S)-1,2-cyclohexylidenedioxyoctadec-3-yne 
• 111394-70-8 (2S)-1,2-O-isopropyliden-octadec-3(Z)-ene-1,2-diol 

Downstream Products

• 131606-88-7 (2S,3E)-1-trityloxyoctadec-3-en-2-ol 
• 131606-90-1 (2S,3E)-2-(2-methoxyethoxymethoxy)-1-trityloxyoctadec-3-ene 

Relevant academic research and scientific papers

First Total Synthesis of Symbioramide, a Novel Ca2+-ATPase Activator from Symbiodinium sp.

The first total synthesis of symbioramide (1) is described and simultaneously established the complete stereostructure of 1 to be (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine.

Total syntheses of symbioramide derivatives from L-serine and their antileukemic activities

Naturally occurring symbioramide, (2S,3R,2′R,3′E)-N-(2′-hydroxy-3′-octadecenoyl)- dihydrosphingosine 1a, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2′S,3′E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2′R,3′Z)-1c and (2S,3R,2′S,3′Z)1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2′S)-isomers of acid parts are more active than those of (2′R)-isomers.

Total Synthesis of Symbioramide, a Novel Ca(2+)-ATPase Activator from Symbiodinium sp.

The first total synthesis of symbioramide 1 has been accomplished by the coupling of D-erythro-dihydrosphingosine with an unusual, chiral α-hydroxy-β,γ-unsaturated fatty acid prepared from L-ascorbic acid, and simultaneously established the complete stereostructure of 1 to be (2S,2'R,3R,3'E)-N-(2'-hydroxyoctadec-3'-enoyl)dihydrosphingosine.