115140-08-4

Basic information

• Product Name: (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene
• Synonyms: (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene
• CAS NO: 115140-08-4
• Molecular Weight: 308.377
• Mol File: 115140-08-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene(115140-08-4)
• EPA Substance Registry System: (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene(115140-08-4)

Safety Data

• Hazardous Substances Data: 115140-08-4(Hazardous Substances Data)

Upstream product

• 14642-79-6 benzyloxy-trimethylsilane 
• 88708-22-9 (+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one 
• 95530-78-2 7-oxabicyclo[2.2.1]hept-5-en-2-one 
• 100-51-6 benzyl alcohol 

Downstream Products

• 123190-65-8 (1S,4S,5S,6S)-6-Benzyloxy-5-bromo-7-oxa-bicyclo[2.2.1]heptan-2-one 
• 115140-20-0 (+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one 
• 139391-31-4 (1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one 
• 139391-31-4 (1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one 
• 223677-23-4 (-)-6-exo-<(tert-butyl)dimethylsilyloxy>-7-endo-benzyloxy-8-oxabicyclo<3.2.1>oct-3-en-2-one 
• 368445-90-3 (1S,2S,4R,5S,6R,7S)-7-endo-(benzyloxy)-8-oxo-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate 
• 368445-79-8 (1S,2R,4R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-one 
• 223677-25-6 (1R,2S,4R,5S,6S,7R,8R)-7-endo-(benzyloxy)-8-exo-hydroxy-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate 
• 368445-80-1 (1S,2S,4S,5R,6R,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]nonan-5-endo-ol 
• 368445-78-7 (1S,2S,4R,5R,6S,7S,8R)-7-endo-(benzyloxy)-8-exo-{[(tert-butyl)dimethylsilyl]oxy}-3,9-dioxatricyclo[4.2.1.0^2,4]non-5-endo-yl benzoate 
• 368446-12-2 methyl (7S)-3,5,7-tri-O-acetyl-7-C-[(1R,2S,3R,4S,5R,7S)-2-endo-(acetyloxy)-7-endo-(benzyloxy)-6-oxo-4-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl]-2,6-anhydro-4-O-benzoyl-L-glycero-D-manno-heptonate 
• 368446-09-7 methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate 

Relevant articles and documents

Acid-Catalyzed Rearrangement of 5,6-exo-Epoxy-7-oxabicyclohept-2-yl Derivatives. Migratory Aptitudes of Acyl vs. Alkyl Groups in Wagner-Meerwein Transpositions

In the presence of HSO3F/Ac2O in CH2Cl2, 2-exo- and 2-endo-cyano-5,6-exo-epoxy-7-bicyclohept-2-yl acetates (6a,b) gave products derived from the epoxide-ring opening and a 1,2-shift of the unsubstituted alkyl group (? bond C(3)-C(4)).In contrast, under similar conditions, the 5,6-exo-epoxy-7-oxabicycloheptan-2-one (6c) gave 5-oxo-2-oxabicycloheptane-3,7-diyl diacetates 20 and 21 arising from the 1,2-shift of the acyl group.Acid treatment of 5,6-exo-epoxy-2,2-dimethoxy-7-oxabicycloheptane (6d) and of 5,6-exo-epoxy-2,2-bis(benzyloxy)-7-oxabicycloheptane (6c) gave minor products arising from epoxide ring opening and the 1,2-shift of ? bond C(3)-C(4) and major products (25,29) arising from the 1,3-shift of a methoxy and benzyloxy group, respectively.Under similar conditions, 5,6-exo-epoxy-2,2-ethylenedioxy-7-oxabicycloheptane (6f) gave 1,1-(ethylenedioxy)-2-(2-furyl)ethyl acetate (32, major) and a minor product 33 arising from the 1,2-shift of ? bond C(3)-C(4).The following order of migratory aptitudes for 1,2-shifts toward electron-deficient centers has been established: acyl > alkyl > alkyl α-substituted with inductive electron-withdrawing groups.This order is valid for,competitive Wagner-Meerwein rearrangements involving equilibria between carbocation intermediates with similar exothermicites.