334695-89-5

Upstream product

• 334670-42-7 (1S,2R,3R,4R)-1,4-di-O-benzoyl-3-[(Z)-4-methoxycarbonylbut-2-enyl]-2-(hydroxymethyl)cyclopentane-1,4-diol 
• 213777-19-6 (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol 
• 213777-18-5 (1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane 
• 334670-38-1 (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol 
• 334670-41-6 (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-4-methoxycarbonylbut-2-enyl]cyclopentane-1,4-diol 
• 334670-40-5 (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-hydroxypent-2-enyl]cyclopentane-1,4-diol 
• 334670-39-2 (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol 
• 334670-37-0 (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol 

Downstream Products

• 334670-44-9 (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-[(Z)-4-methoxycarbonylbut-2-enyl]-2-[(E)-3-oxooct-1-enyl]cyclopentane-1,4-diol 
• 334670-46-1 (1S,2S,3R,4R)-1,4-di-O-benzoyl-3-[(Z)-4-methoxycarbonylbut-2-enyl]-2-[(3RS,E)-3-hydroxyoct-1-enyl]cyclopentane-1,4-diol 

Relevant academic research and scientific papers

Total syntheses of four metabolites of 15-F2t-isoprostane

Total syntheses are described of the methyl esters of enantiomers of two major urinary metabolites of 15F2t-isoprostane - 2,3-dinor-5,6-dihydro-15F2t-isoprostane 1 and 2,3-dinor15F2t-isoprostane 2 - together with other, related, putative metabolites (15R)/(15S)-2,3-dinor-5,6,13,14-tetrahydro-15F2tisoprostane 3 and 2,3-dinor-5,6,13,14-tetrahydro-15-oxo 15F2t-isoprostane 4. The synthesis, starting from diacetone d-glucose, includes as its main steps a radical cyclization reaction of highly functionalized precursors, followed by Wittig and/or Horner-Wadsworth-Emmons elongation using phosphorus synthons. The compounds synthesized here have been used as reference compounds for studying the metabolism of 15F2t-isoprostane and ent-15F2t-isoprostane.