80735-00-8

Upstream product

• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 
• 88203-80-9 C₃₅H₃₂N₂O₄ 
• 80685-07-0 (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane 
• 80675-63-4 (1R)-2-endo,3-exo-dibenzoyloxy-4-endo-hydroxymethyl-N-methyl-6-azabicyclo<3.1.0>hexane 
• 71155-05-0 (1R,5S)-bicyclo[3.2.0]hept-2-en-6-one 
• 80675-69-0 (1R,5R)-6-exo,7-endo-dibenzoyloxy-8-exo-iodo-3-oxo-2-oxabicyclo<3.3.0>octane 
• 80675-68-9 C₂₁H₁₈O₆ 
• 80675-67-8 3,4-dibenzoyloxy-5-(formylmethyl)cyclopent-1-ene 
• 80675-65-6 (3R,4R,5R)-3,4-dibenzoyloxy-5-(tosyloxymethyl)cyclopent-1-ene 
• 80675-70-3 (1S,5S)-6-exo,7-endo-dibenzoyloxy-3-oxo-2-oxabicyclo<3.3.0>octane 
• 80675-66-7 C₂₁H₁₇NO₄ 
• 80734-99-2 (1S,5S)-6-exo,7-endo-dihydroxy-3-oxo-2-oxabicyclo<3.3.0>octane 

Relevant academic research and scientific papers

Functionalised Carbocycles from Carbohydrates. Part 3. The Synthesis of the Epoxy Lactone Prostaglandin Intermediate via an Isoxazolidine Derivative. X-Ray Crystal Structure of (1R,5R)-6-exo,7-endo-Dibenzoyloxy-8-exo-iodo-3-oxo-2-oxabicyclooctane

The bicyclic isoxazolidine 6,7-dibenzoyloxy-N-methyl-8-tosyloxy-3-oxa-2-azabicyclooctane (1), which is easily obtained from a readily available D-glucose derivative, has been converted into the epoxy lactone 8-oxo-3,7-dioxatricyclo2,4>nonane (13), via a series of cyclopentane derivatives, in ten steps.Since the product (13) can be used to prepare prostaglandins this sequence represents a new route to these compounds in their enantiomerically pure natural form.

A General Route to Optically Pure Prostaglandins from a D-Glucose Derivative

The epoxy-lactone (14), which is a key intermediate in one synthetic route to prostaglandins, has been prepared from a readily available D-glucose derivative.

NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 15. EPOXIDATION OF OLEFINS WITH DIETHYL PHOSPHOROCYANIDATE (DEPC) AND HYDROGEN PEROXIDE

A mixture of diethyl phosphorocyanidate (DEPC) and hydrogen peroxide in the presence of 2-hydroxypyridine or 1,2,4-triazole functions as an epoxidizing agent for olefins.Keywords: diethyl phosphorocyanidate; hydrogen peroxide; epoxidation; 2-hydroxypyridine; 1,2,4-triazole; peroxyphosphoric acid