170423-00-4

Basic information

• Product Name: 6-Oxabicyclo[3.1.0]hexane-2-carboxylicacid,methylester,(1alpha,2beta,5alpha)-(9CI)
• Synonyms: 6-Oxabicyclo[3.1.0]hexane-2-carboxylicacid,methylester,(1alpha,2beta,5alpha)-(9CI)
• CAS NO: 170423-00-4
• Molecular Formula: C7H10O3
• Molecular Weight: 142.15
• Product Categories: CARBOXYLICESTER
• Mol File: 170423-00-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Oxabicyclo[3.1.0]hexane-2-carboxylicacid,methylester,(1alpha,2beta,5alpha)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxabicyclo[3.1.0]hexane-2-carboxylicacid,methylester,(1alpha,2beta,5alpha)-(9CI)(170423-00-4)
• EPA Substance Registry System: 6-Oxabicyclo[3.1.0]hexane-2-carboxylicacid,methylester,(1alpha,2beta,5alpha)-(9CI)(170423-00-4)

Safety Data

• Hazardous Substances Data: 170423-00-4(Hazardous Substances Data)

Upstream product

• 2258-56-2 methyl cyclopent-2-ene-1-carboxylate 

Downstream Products

• 170422-96-5 methyl c-2-hydroxy-t-3-methyl-r-1-cyclopentancarboxylate 
• 170422-97-6 methyl c-3-hydroxy-t-2-methyl-r-1-cyclopentancarboxylate 
• 162086-59-1 3-hydroxy-cyclopentene-1-carboxylic acid methyl ester 
• 170422-96-5 methyl t-2-hydroxy-c-3-methyl-r-1-cyclopentanecarboxylate 
• 170422-97-6 (1S,2S,3S)-3-Hydroxy-2-methyl-cyclopentanecarboxylic acid methyl ester 

Relevant articles and documents

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 9. Synthesis and ring opening reactions of cis- and trans-oxides derived from 3-(benzyloxymethyl)cyclopentene and methyl 2- cyclopenten-1-carboxylate

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the oxirane systems derived from cyclopentene bearing a polar functionality (CH2OBn or COOMe) in a homoallylic relationship to the oxirane ring. The cis/trans diastereoisomeric epoxide pairs 7-8 and 9-10 derived from 3- (benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate, respectively, were prepared and some of their opening reactions were studied. The regioselectivity observed turned out to depend on the opening reaction protocol (standard or metal-assisted), suggesting the efficacious incursion, under the appropriate conditions, of chelate bidentate species in the opening process.

ASYMMETRIC TOTAL SYNTHESIS OF STOECHOSPERMOL USING INTRAMOLECULAR (2+2) PHOTOCYCLOADDITION REACTION

The first asymmetric total synthesis of stoechospermol, a representative spatane diterpene having cis, anti, cis-tricyclo2,6>decane ring system, was achieved.Using the intramolecular asymmetric (2+2) photocycloaddition reaction of the diastereomeric ester 11, the readily available butenolide 9 was transformed into the optically active dilactone 12a and 12b.Subsequent construction of tricyclic carbon ring system and introduction of substituents in a right stereochemistry gave rise to optically pure stoechospermol 1.