171017-05-3

Upstream product

• 764-93-2 1-decyne 
• 70639-22-4 (2S,3S)-1,2-Epoxy-3-methylpentane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 171017-02-0 (12R,13S)-13-Methylpentadec-1-yn-12-ol 
• 171017-03-1 (12R,13S)-12-tert-Butyldimethylsilyloxy-13-methylpentadec-1-yne 
• 171017-04-2 tert-Butyl (4S)-4-<(1'R,13'R,14'S)-13'-tert-butyldimethylsilyloxy-1'-hydroxy-14'-methylhexadec-2'-ynyl>-2,2-dimethyloxazolidine-3-carboxylate 
• 171017-10-0 (3S,4R)-3-Methylpentadec-6-yn-4-ol 
• 187100-37-4 (E)-(2S,3R,15R,16S)-2-Amino-15-(tert-butyl-dimethyl-silanyloxy)-16-methyl-octadec-4-ene-1,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 171017-11-1 (2S,3R,15R,16S,4E)-2-Amino-1,3,15-tris-tert-butyldimethylsilyloxy-16-methyloctadec-4-ene 

Downstream Products

• 171017-06-4 (2S,3S,4R,5S,15R,16S)-1,3,15-Tris-tert-butyldimethylsilyloxy-4,5-epoxy-16-methyl-2-p-tolylsulfonylaminooctadecane 
• 171017-12-2 (2S,3S,4R,15R,16S)-1,3,15-Tris-tert-butyldimethylsilyloxy-16-methyl-2-p-tolylsulfonylaminooctadecan-4-ol 
• 171017-07-5 (2S,3S,4R,15R,16S)-1,3,15-Tris-tert-butyldimethylsilyloxy-16-methyl-2-p-tolylsulfonylaminooctadecan-4-yl mesylate 
• 187100-45-4 (2S,3R,4S,11'R,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine 

Relevant academic research and scientific papers

Synthesis of sphingosine relatives. Part 19. Synthesis of penaresidin A and B, azetidine alkaloids with actomyosin ATPase-activating properties

Three stereoisomers of penaresidin A 1 and two stereoisomers of penaresidin B 2' (Scheme 5), azetidine alkaloids isolated from the Okinawan marine sponge Penares sp., have been synthesized.In the course of our synthetic study, the correct structure of penarisidin B has been shown to be not 2 but 2'.Natural penaresidin A is either (2S,3R,4S,15S,16S)- or (2S,3R,4S,15R,16R)-1 and natural penaresidin B is either (2S,3R,4S,15S)- or (2S,3R,4S,15R)-2'.

Synthesis of penaresidin A, an azetidine alkaloid with actomyosin ATPase-activating property

Three stereoisomers of pentaresidin A (1) an azetidine alkaloid isolated from the Okinawan marine sponge Penares sp., were synthesized. The natural penaresidin A must be either (2S,3R,4S,15S,16S)- or (2S,3R,4S,15R,16R)-1.