261775-39-7

Upstream product

• 1026249-12-6 (E)-6-Benzyloxy-3-hydroxy-4-methyl-hex-4-enoic acid ethyl ester 
• 101376-74-3 (E)-4-(benzyloxy)-2-methylbut-2-enal 
• 261775-38-6 6-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-en-3-ol 

Downstream Products

• 261775-49-9 (R)-1-((2S,3S)-3-Benzyloxymethyl-2-methyl-oxiranyl)-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol 
• 261775-50-2 (2R,3S,4R)-1-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hexane-2,4-diol 

Relevant academic research and scientific papers

Diastereoselective opening of trisubstituted epoxy alcohols: Application in the studies directed toward the synthesis of octenoic acid moiety of cryptophycins

Stereoselective synthesis of the 5,7-acetonide of (2E,5S,6R,7R,8S)-5,7,8-trihydroxy-6-methyl-8-phenyl-2-octenoic acid ethyl ester (3), an isomer of 2, precursor of the epoxy octenoic acid moiety 1 present in depsipeptide cryptophycins is achieved where diastereoselective opening of an intermediate trisubstituted epoxy alcohol 4 based on a radical-mediated method developed by us earlier furnishes the crucial '2-methyl-1,3-diol' moiety of the C5-C7 segment of the molecule. The protocol also allows the synthesis of some of the other 16 diasteromers of this hydroxy acid having 4 chiral centres which can find useful applications in the structure-activity relationship (SAR) studies of these potent antitumor agents.