150311-80-1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 150311-79-8 ethyl 11(S),12(R)-O-isopropylidene-11,12,13(R)-trihydroxy-octadeca-9,15(Z)-dienoate 
• 1055042-95-9 (Z)-10-{(4R,5S)-5-[(Z)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester 
• 143396-27-4 [(R)-1-((4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-3-ynyloxy]-tert-butyl-dimethyl-silane 
• 143360-28-5 [(Z)-(R)-1-((4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-3-enyloxy]-tert-butyl-dimethyl-silane 
• 143396-26-3 (2R,3S,4R)-1-benzyloxy-4-tert-butyldimethylsilyloxy-2,3-O-isopropylidenehept-6-yne-2,3-diol 
• 150255-64-4 (Z)-4-O-tert-butyldimethylsilyl-5,6,7,8,9-pentadeoxy-2,3-O-isopropylidene-arabino-non-6-enose 
• 143396-29-6 {(4R,5S)-5-[(Z)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 143396-25-2 (2R,3R,4R)-1-benzyloxy-2,3-O-isopropylidenehept-6-yne-2,3,4-triol 
• 81801-09-4 4-O-benzyl-2,3-O-isopropylidene-D-threose 
• 150311-79-8 (Z)-10-[(4R,5R)-5-((Z)-(R)-1-Hydroxy-hex-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-dec-9-enoic acid ethyl ester 

Downstream Products

• 221633-52-9 (11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of methyl (11S,12S,13S)-(9Z,15Z)-11-hydroxy-12,13-epoxy octadecadienoate from D-mannose

The title compound, a self defensive substance against the rice blast disease, was synthesized from D-mannose in ten steps. The key intermediate 6 was prepared with Grignard addition of lactol 5 in favoured anti-selectivity.

Stereoselective Syntheses of Two Constituents Against Rice Blast Disease

(11S,12S,13S)-Trihydroxy-(9Z,15Z)-octadecanoic acid 1 and methyl (11R,12S,13S)-11-hydroxy-12,13-epoxyoctadecadienoate 3a were synthesized starting from L-(+)- and D-(-)-tartaric acids, respectively.