80675-68-9

Upstream product

• 80675-67-8 3,4-dibenzoyloxy-5-(formylmethyl)cyclopent-1-ene 
• 88203-86-5 (1S,5S)-2-exo,3-endo-dibenzoyloxy-6-exo-hydroxy-4-exo-tosyloxybicyclo<3.2.0>heptane 
• 88203-87-6 (1S,5R)-2-exo,3-endo-dibenzoyloxy-6-oxo-4-exo-tosyloxybicyclo<3.2.0>heptane 
• 88203-83-2 (3E,5S,6S,7R)-6,7-dibenzoyloxy-5-tosyloxynona-3,8-dien-2-one 
• 80685-07-0 (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 
• 80675-65-6 (3R,4R,5R)-3,4-dibenzoyloxy-5-(tosyloxymethyl)cyclopent-1-ene 
• 80675-66-7 C₂₁H₁₇NO₄ 
• 80675-63-4 (1R)-2-endo,3-exo-dibenzoyloxy-4-endo-hydroxymethyl-N-methyl-6-azabicyclo<3.1.0>hexane 
• 88203-85-4 (1S,5S)-6-exo-acetoxy-2-exo,3-endo-dibenzoyloxy-4-exo-tosyloxybicyclo<3.2.0>heptane 
• 88203-82-1 (1S,5S)-6-exo-acetyl-2-exo,3-endo-dibenzoyloxy-4-exo-tosyloxybicyclo<3.2.0>heptane 
• 88203-80-9 C₃₅H₃₂N₂O₄ 

Downstream Products

• 80675-69-0 (1R,5R)-6-exo,7-endo-dibenzoyloxy-8-exo-iodo-3-oxo-2-oxabicyclo<3.3.0>octane 
• 80735-00-8 (1S,2R,4S,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 
• 80675-70-3 (1S,5S)-6-exo,7-endo-dibenzoyloxy-3-oxo-2-oxabicyclo<3.3.0>octane 
• 59829-44-6 (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane 

Relevant academic research and scientific papers

Functionalised Carbocycles from Carbohydrates. Part 4. The Synthesis of the Epoxy Lactone Prostaglandin Intermediate via Bicycloheptane Derivatives. X-Ray Crystal Structure of (1R)-5-endo-Acetyl-2-exo,3-endo-dibenzoyloxybicycloheptane

Irradiation of the nona-3,8-dienulose derivative (2) at 350 nm gave the bicycloheptyl methyl ketone (3) in good yield.This was converted via the acetate (5) into the corresponding bicycloheptanol (6) which, with base, gave the cyclopentenyl aldehyd

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.