80675-69-0

Upstream product

• 88203-95-6 (1S,5S)-2-exo,3-endo-dibenzoyloxy-4-exo-iodo-6-oxobicyclo<3.2.0>heptane 
• 80675-68-9 C₂₁H₁₈O₆ 
• 80675-66-7 C₂₁H₁₇NO₄ 
• 80675-65-6 (3R,4R,5R)-3,4-dibenzoyloxy-5-(tosyloxymethyl)cyclopent-1-ene 
• 80675-67-8 3,4-dibenzoyloxy-5-(formylmethyl)cyclopent-1-ene 
• 88203-93-4 (1'R,2'R,4'S,5'R,6'S)-5'-hydroxy-3'-oxaspiro<<1,3>-dithiolane-2,8'-tricyclo<4.2.0.0^2,4>octane> 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 
• 80675-63-4 (1R)-2-endo,3-exo-dibenzoyloxy-4-endo-hydroxymethyl-N-methyl-6-azabicyclo<3.1.0>hexane 
• 88203-94-5 (1S,5S)-2-exo,3-endo-dibenzoyloxy-4-exo-iodospiroheptane-6,2'-<1,3>-dithiolane> 
• 88203-92-3 (1S,5R)-2-exo,3-endo-dibenzoyloxy-4-exo-tosyloxyspiroheptane-6,2'-<1,3>-dithiolane> 
• 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 

Downstream Products

• 80675-70-3 (1S,5S)-6-exo,7-endo-dibenzoyloxy-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 
• 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 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.

Functionalised Carbocycles from Carbohydrates. Part 5. The Synthesis of the Epoxybicycloheptanone Ethylene Acetal Prostaglandin Intermediate

Treatment of the ethylene dithioacetal (4) of the bicycloheptanone derivative (3) with base gave specifically the hydroxy epoxide (8) which, with most nucleophiles, reacted at C-2, to give analogues of the starting material (4).The iodo dibenzoate

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

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.