26115-01-5

Usage

Uses

Used in Organic Synthesis:
6ALPHA, 7ALPHA-EPOXY-2-OXABICYCLO[3.3.0]OCTAN-3-ONE is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its epoxy and ketone functional groups provide versatility in chemical reactions, allowing for the formation of a wide range of products.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6ALPHA, 7ALPHA-EPOXY-2-OXABICYCLO[3.3.0]OCTAN-3-ONE is used as a building block for the development of new pharmaceuticals. Its unique structure and functional groups can be exploited to create novel drug candidates with potential therapeutic applications.
Used in Research and Development:
6ALPHA, 7ALPHA-EPOXY-2-OXABICYCLO[3.3.0]OCTAN-3-ONE is utilized in research and development for the exploration of its properties and potential applications. Further studies are needed to fully understand its capabilities and to identify new uses in various industries.

Upstream product

• 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 
• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 80685-07-0 (1R,5R)-6-exo,7-endo-dibenzoyloxy-N-methyl-8-exo-tosyloxy-3-oxa-2-azabicyclo<3.3.0>octane 
• 88203-80-9 C₃₅H₃₂N₂O₄ 
• 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 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Relevant academic research and scientific papers

Tandem transformations of cyclopentene α,α-dichlorocarboxamides into epoxy lactones induced by a γ-hydroxyl group; A short synthesis of the Corey epoxy lactone and its enantiomer

The stable iminolactone 6 was obtained by NBS induced bromocyclization of carboxamide 4. Under treatment of 6 with DBU a tandem recyclization transformation occurred resulting in the formation of epoxyiminolactone 7. Bromo(iodo)cyclization of 4 in aqueous organic medium followed by treatment with base gave epoxylactone 9. Under the optimized conditions, Corey epoxylactone 1 and its enantiomer ent-1 were obtained from diastereomeric carboxamides 4 and 5 in an overall yield of 40%.

Haloiminolactonization of cyclopentene α,α-dichlorocarboxamides. Tandem rearrangement of iminolactones in epoxylactones

Electrophilic cyclization initiated by NBS and I2 of 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxy-2-cyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides was investigated. Stable under conditions of chromatography on SiO2 bicyclic iminoesters, (2Z,3aS,4S,6S,6aS)-6-bromo-3,3-dichloro- and (2Z,3aS,4S,6S,6aS)-3,3-dichloro-6-iodo-2-{[(1R)-1-phenylethyl]imino}hexahydro-2H-cyclopenta[b]furan-4-ols were isolated and characterized, and a possible version was suggested of their step-by-step recyclization transformations. The halocyclization of carboxamides in water-organic mixtures afforded bicyclic epoxylactones (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-5,5-dichlorohexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones, whose reductive dechlorination proceeded stepwise with successive removal of Cl atoms and led to the formation of (1aR,2aS,5aS,5bS)- and (1aS,2aR,5aR,5bR)-hexahydro-4H-oxireno[3,4]cyclopenta-[1,2-b]furan-4-ones.

Bromohydrin reactions of Grieco's bicyclic lactone

The bromohydrin reaction in Grieco's bicyclic lactone 1 was reinvestigated. Two regioisomeric bromohydrins were obtained (2 and 8), and their configurations were unambiguously determined by X-ray diffraction analyses.

SYNTHESIS OF NOVEL BICYCLIC ALCOHOLS AND THEIR NITRATES

1(R),5(S)-2-oxa-bicyclooct-6-en-3-one (2), a chiral by-product of the manufacture of prostaglandin derivatives, is easily converted into the alcohols (5a), (6a), (6c) and nitrates (5b), (6b), and (6d).Regio- and stereoisomers were identified on the basis of their NMR spectra.

Total synthesis of a potent thromboxane A2 antagonist

The synthesis of the powerful thromboxane A2 antagonist 3 (EC50 3 nM) is reported.

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.

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

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.