113331-85-4

Upstream product

• 113331-81-0 (1R^*,4R^*,5S^*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane 
• 113331-81-0 (1R,4R,5R)-5-Phenyl-2,3-dioxa-bicyclo[2.2.1]heptane 
• 27856-20-8 1-hydroxy-3-phenylcyclopent-3-ene 
• 29586-29-6 1-acetoxy-3-phenyl-3-cyclopentene 
• 113331-83-2 4-bromo-2-phenyl-1-cyclopentylhydroperoxide 
• 114738-33-9 (1R^*,3R^*,4S^*)-1-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-4-phenylcyclopentane 
• 120624-02-4 (1RS,2SR,4RS)-4-acetoxy-2-phenyl-1-cyclopentanol 
• 114738-46-4 (1RS,3SR,4SR)-1,3-diacetoxy-4-phenylcyclopentane 
• 114738-33-9 (1S^*,3R^*,4S^*)-1-acetoxy-3-<(tert-butyldimethylsilyl)oxy>-4-phenylcyclopentane 
• 120624-03-5 (1SR,3SR,4SR)-1-acetoxy-3-bromo-4-phenylcyclopentane 
• 120624-02-4 (1RS,2SR,4SR)-4-acetoxy-2-phenyl-1-cyclopentanol 
• 113331-82-1 1-bromo-3-phenyl-3-cyclopentene 
• 113331-85-4 (1R^*,3R^*,4S^*)-4-phenylcyclopentane-1,3-diol 
• 591-51-5 phenyllithium 

Downstream Products

• 27856-20-8 1-hydroxy-3-phenylcyclopent-3-ene 
• 19926-46-6 1-hydroxy-3-phenylcyclopent-2-ene 
• 113331-85-4 (1S^*,3S^*,4S^*)-4-phenylcyclopentane-1,3-diol 
• 114738-39-5 1-hydroperoxy-3-phenylcyclopent-2-ene 
• 114738-38-4 1-hydroperoxy-3-phenylcyclopent-3-ene 
• 113331-81-0 (1R^*,4R^*,5S^*)-5-phenyl-2,3-dioxabicyclo<2.2.1>heptane 
• 114738-46-4 (1R^*,3R^*,4S^*)-1,3-diacetoxy-4-phenylcyclopentane 

Relevant academic research and scientific papers

SYNTHESIS OF A PROSTAGLANDIN ENDOPEROXIDE MODEL COMPOUND AND ITS REACTION WITH ELECTRON TRANSFER REAGENTS

5-Exo-phenyl-2,3-dioxabicycloheptane (4c) was synthesized as a model compound of prostaglandin endoperoxide (PGH) to mimic the bioconversion of PGH into thromboxane (TX).The reaction of (4c) with various electron transfer reagents was investigated.With the aid of a catalytic amount of ferrous ion, (4c) was successfully converted into the thromboxane B (TXB) skeleton.

Formation of 1-Phenyl-2,3-dioxabicycloheptane in the Reaction of 1,3-Dibromo-4-phenylcyclopentane with Hydrogen Peroxide in the Presence of Silver Trifluoroacetate

Reaction of 1,3-dibromo-4-phenylcyclopentane (23), prepared from 4-hydroxycyclopent-2-en-1-one (10) in a stereocontrolled manner, or its stereoisomer 24 with anhydrous hydrogen peroxide in the presence of silver trifluoroacetate in ether gave 1-phenyl-2,3-dioxabicycloheptane (25) mainly as a rearranged product.The expected 5-phenyl-2,3-dioxabicycloheptane (8) and phenylcyclopentenyl hydroperoxides 26 and 27 were also formed in this reaction.An authentic sample of endoperoxide 8 was prepared by using peroxide transfer reaction between bis(tri-n-butyltin)peroxide and bistriflate of cis-diol 35.The stereochemistry of the endoperoxide 8 and related compounds in this series was confirmed by correlation with the data from X-ray crystallographic analysis of the diacetate of diol 21 obtained from endoperoxide 8 by stannous chloride reduction.

An Electron Transfer Model for Thromboxane Biosynthesis

Conversion of prostaglandin endoperoxide model compound (1) into the thromboxane B ring system (6a) and (7a) was achieved with the aid of the ferrous ion.