137567-91-0

Basic information

• Product Name: (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one
• Synonyms: (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one
• CAS NO: 137567-91-0
• Molecular Weight: 138.166
• Mol File: 137567-91-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one(137567-91-0)
• EPA Substance Registry System: (+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one(137567-91-0)

Safety Data

• Hazardous Substances Data: 137567-91-0(Hazardous Substances Data)

Upstream product

• 34638-25-0 (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 74-88-4 methyl iodide 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 

Downstream Products

• 1321531-35-4 (3R,3aR,5R,6aR)-3-methylhexahydro-2H-cyclopenta[b]-furan-5-yl (4-nitrophenyl)carbonate 
• 1321531-22-9 (3R,3aR,5R,6aR)-3-methylhexahydro-2H-cyclopenta[b]-furan-5-yl [(2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl]carbamate 
• 286408-54-6 (1R,3S,4S,5R,6S,7S)-3-methoxy-4,6-dimethyl-7-[4-methoxybenzyloxy]-2-oxabicyclo[3.3.0]-octane 
• 286408-56-8 (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol 
• 286408-57-9 (2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone 
• 286408-55-7 (1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol 

Relevant articles and documents

C-3 SUBSTITUTED BICYCLOOCTANE BASED HIV PROTEASE INHIBITORS

C3-functionalized-cyclopentanyltetrahydrofuranyl carbamates that inhibit HIV proteolytic enzymes and processes for preparing the compounds are described. Compositions comprising the disclosed compound and methods of using the compounds and/or compositions for treating patients infected with HIV are also described.

Synthesis of the C1-C9 fragment of callipeltoside-A

(Equation presented) The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

Microbial Oxidation of 7endo-Methylbicyclohept-2-en-6-one, 7,7-Dimethylbicyclohept-2-en-6-one and 2exo-Bromo-3endo-hydroxy-7,7-dimethylbicycloheptan-6-one using Acinetobacter NCIMB 9871

A bio-Bayer-Villiger reaction using Acinetobacter NCIMB 9871 and the bicycloheptanone 2 provided the corresponding substituted oxabicyclooctanones 6 and 7.Similarly the ketones 3 and 9 furnished the lactones 8 and 10 respectively: the lactones 6, 7 and 10 were obtained in states of high optical purity.