59829-44-6

Basic information

• Product Name: (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane
• Synonyms: (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane
• CAS NO: 59829-44-6
• Molecular Weight: 140.139
• Mol File: 59829-44-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane(59829-44-6)
• EPA Substance Registry System: (1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo<4.3.0.0^2,4>nonane(59829-44-6)

Safety Data

• Hazardous Substances Data: 59829-44-6(Hazardous Substances Data)

Upstream product

• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 80675-66-7 C₂₁H₁₇NO₄ 
• 80675-70-3 (1S,5S)-6-exo,7-endo-dibenzoyloxy-3-oxo-2-oxabicyclo<3.3.0>octane 
• 80675-65-6 (3R,4R,5R)-3,4-dibenzoyloxy-5-(tosyloxymethyl)cyclopent-1-ene 
• 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 
• 80734-99-2 (1S,5S)-6-exo,7-endo-dihydroxy-3-oxo-2-oxabicyclo<3.3.0>octane 
• 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 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 

Relevant articles and documents

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.

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.