68376-88-5

Usage

InChI:InChI=1/C18H30O6/c1-2-3-4-5-12(19)6-8-14-15(17(22)11-16(14)21)10-13(20)7-9-18(23)24/h14-17,21-22H,2-11H2,1H3,(H,23,24)/t14-,15-,16-,17+/m0/s1

Upstream product

• 82290-28-6 13,14-dihydro-2,3-dinor-6,15-dioxo-PGF₁α 6,9-hemiacetal 1,6-lactone 
• 37786-09-7 11,15-bis(tetrahydro-2H-pyran-2-yl)-prostaglandin F_2α 
• 82290-26-4 2,3-dinor-6-oxo-PGF₁α 6,9-hemiacetal 1,6-lactone 
• 82290-25-3 5-[(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-4-oxo-pentanoic acid 
• 82290-24-2 5-(tert-Butyl-dimethyl-silanyloxy)-1-{(1R,2R,3R,5S)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-pentan-2-one 
• 82290-23-1 (1S,2R,3R,4R)-2-[(Z)-5-(tert-Butyl-dimethyl-silanyloxy)-pent-2-enyl]-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentanol 
• 82290-27-5 2,3-dinor-6,15-dioxo-PGF₁α 6,9-hemiacetal 1,6-lactone 
• 82290-21-9 Acetic acid (1S,2R,3R,4R)-2-[5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentyl]-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl ester 
• 82290-18-4 (1S,2R,3R,4R)-2-((Z)-5-Hydroxy-pent-2-enyl)-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentanol 

Relevant academic research and scientific papers

The synthesis of 2,3-dinorprostacyclin metabolites - A new approach to spirolactone hemiacetals

The major human urinary metabolites of prostacyclin and 6-keto-PGF1α have been synthesized by a direct route, involving three-carbon homologation of bicyclic lactone intermediates and spontaneous spirolactonization of the products. The fact that these 2,3-dinor-6-oxo metabolites exist almost exclusively as spirolactone hemiacetals under acidic conditions (pH 5 and below) may explain the reported difficulties in derivatizing samples of biological origin. Several 19,19.20,20-d4 metabolites have also been synthesized.