470690-27-8

Basic information

• Product Name: (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol
• Synonyms: (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol
• CAS NO: 470690-27-8
• Molecular Weight: 550.811
• Mol File: 470690-27-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol(470690-27-8)
• EPA Substance Registry System: (-)-(S)-[(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-(2-hydroxymethylcyclohex-1-enyl)methanol(470690-27-8)

Safety Data

• Hazardous Substances Data: 470690-27-8(Hazardous Substances Data)

Upstream product

• 470690-24-5 (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(1S)-3-oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-22-3 (+)-(1R,2S,4R,5S)-1-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-23-4 (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-17-6 (+)-(1R,2S,4R,5S)-1-(tert-butyldiphenylsilyloxy)-1-formyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 470690-20-1 (+)-(1R,2S,4S)-1-(tert-butyldimethylsilyloxymethyl)-3,3-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 470690-42-7 (1R,5S,7S)-3-[(1R)-2-chloro-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one 
• 139437-47-1 (R)-2-{[1-Furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-ethanol 
• 470690-19-8 (1R,2S,4S)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 
• 301823-95-0 (+)-(1R,5S,7S)-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.o^1,5]dec-8-en-4-one 
• 77704-39-3 (-)-(1R,5S,7S)-3-[(1R)-2-hydroxy-1-phenylethyl]-6,6-dimethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-en-4-one 
• 77704-70-2 (-)-(R)-N-<(Furan-2-yl)methyl>-N-(2-hyydroxy-1-phenylethyl)-3-methylbut-2-enamid 
• 132168-60-6 (-)-(R)-2<<(Furan-2-yl)methyl>amino>-2-phenylethanol 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 98-01-1 furfural 

Downstream Products

• 470690-30-3 (-)-(S)-acetic acid [(1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)-2-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-hydroxymethylcyclohex-1-enyl)methyl ester 
• 470690-29-0 (-)-(S)-acetic acid [(1R,2R,4R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl][2-(tert-butyldimethylsilyloxymethyl)cyclohex-1-enyl]methyl ester 
• 470690-28-9 (-)-(S)-[(1R,2R,4R,5S)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptan-1-yl][2-(tert-butyldimethylsilyloxymethyl)cyclohex-1-enyl]methanol 

Relevant articles and documents

Studies towards the total synthesis of solanoeclepin A: Synthesis of the 7-oxabicyclo[2.2.1]heptane moiety and attempted seven-membered ring formation

This paper details studies towards the total synthesis of solanoeclepin A (1), the most active natural hatching agent of potato cyst nematodes. The first goal was the preparation of the tetracyclic left-handed substructure 2 in enantiopure form. The 7-oxabicyclo[2.2.1]heptane moiety was obtained via a diastereoselective intramolecular Diels-Alder strategy by using (R)-phenylglycinol as a chiral auxiliary as pioneered by Mukaiyama. A chromium-mediated nickel-catalysed coupling of aldehyde 5 with vinyl triflate 6 gave α,β-unsaturated lactone 18 as a single stereoisomer. The seven-membered ring was expected to arise from a McMurry coupling of dialdehyde 4. Surprisingly, oxidation of diol 24 did not lead to the desired dialdehyde 4, but to the eight-membered ring lactone 25.