104855-40-5

Upstream product

• 104973-58-2 (2S,3S)-2-(acetyloxy)-3-methylpentanoic acid 
• 100-51-6 benzyl alcohol 
• 73-32-5 L-isoleucine 

Downstream Products

• 40297-93-6 (S)-2-Hydroxy-(S)-3-methylpentanoic acid benzyl ester 
• 135677-47-3 benzyl (2R,3S)-2-((tert-butyldimethylsilyl)oxy)-3-methylpentanoate 
• 114029-77-5 Methyl (9S),10-Epoxy-(8R)-((2'R)-tert-butyldiphenylsilyloxy-(3'S)-methylpentanoyloxy)-9-methyl-deca-(E,E,E)-trienoate 
• 104855-42-7 (2E,4E,6Z)-(R)-8-[(2R,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester 
• 104881-82-5 Benzyl (2R)-(tert-Butyldiphenylsilyloxy)-(3S)-methylpentanoate 
• 113956-83-5 (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid 
• 113956-82-4 benzyl (2R,3S)-2-hydroxy-3-methylpentanoate 
• 113956-81-3 benzyl (2R,3S)-2-formyloxy-3-methylpentanoate 
• 104855-42-7 (2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester 
• 104855-43-8 (2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid 
• 104855-43-8 (2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid 
• 104363-99-7 AF-toxin II_c 
• 104855-42-7 Methyl (9S),10-Epoxy-(8R)-((2'S)-tert-butyldiphenylsilyloxy-(3'S)-methylpentanoyloxy)-9-methyl-deca-(E,E,E)-trienoate 
• 104881-82-5 Benzyl (2S)-(tert-butyldiphenylsilyloxy)-(3S)-methylpentanoate 

Relevant academic research and scientific papers

Synthesis of methyl esters of AF-toxin IIa and IIc, toxins to Japanese white pear produced by Alternaria alternata strawberry pathotype

Methyl esters of AF-toxin IIa and IIc, toxic compounds to Japanese white pear produced by Alternaria alternata strawberry pathotype, were synthesized as the optically active forms starting from vitamin C as a chiral material.

Syntheses of the Ethyl Esters of the Plant Host-Selective (H-S) Toxins (AF-IIa, AF-IIc and AK-II) Produced by Pathotypes of Alternaria alternata

Total syntheses of the ethyl esters of the host-selective (H-S) toxins produced by Alternaria alternata (strawberry-type pathogen), AF-IIa and AF-IIc, and by the Japanese pear-type AK-II are reported.The initial synthetic objectives, the 2E,4E,6E, 2E,4Z,6E and 2E,4E,6Z stereoisomers of ethyl 8-hydroxy-9-methyldeca-2,4,6,9-tetraenoate, were attained by the use of acetylene hydrometallation and Pd0-mediated vinyl halide coupling: for this purpose tin chemistry was superior to the use of zirconium compounds.The tetraene-hydroxy esters were epoxidised selectively at the 9,10-double bond by the Sharpless procedure under conditions of kinetic control (50percent reaction), which it was predicted would lead to products of predominantly (8R,9S)-stereochemistry.Esterification of the epoxides produced from the 2E,4E,6E and 2E,4E,6Z hydroxy esters with synthetic (2R,3S)-2-(t-butyldimethylsiloxy)-3-methylpentanoic acid, followed by HPLC separation, gave as the major products, stereoisomers which, after deprotection, were characterised as the ethyl esters AF-toxin IIc and AF-toxin IIa.The stereochemical nature of the minor products in the epoxidations is considered.For the sythesis of the AK-II toxin as its ethyl ester, similar esterification with N-acetyl-L-phenylalanine was carried out, except that the racemisation of the amino acid centre ensued.This led to two major products which were separated and identified as (8R,9S,2'S)- and (8R,9S,2'R)-stereoisomers, the former being identical with the ester of AK-II toxin.