Synthesis of Octoses by Brimacombe Methodology; a Hard Proof for the Structure of the anti-Kishi Product of Osmylation of Unsaturated Ester

• Autorzy: Jarosz S. , Osuch A. , Luboradzki R.
• Języki publikacji: EN

Abstrakty

EN

Reaction of 1,2:3,4-di-O-isopropylidene--D-galactopyranos-6-ulose with Ph3P=CH-CO2Me conducted in methanol afforded exclusively the Z-,-unsaturated ester, which was further reduced with DIBAL-H to the allylic alcohol. Osmylation of the unsaturated ester afforded two stereoisomeric diols in a 4:1 ratio, with the ‘anti Kishi product’ predominating, while the same process performed on the allylic alcohol provided the expected ‘Kishi product’with high selectivity. The structure of the latterwas confirmed byX-ray analysis of its 8-O-tritylated derivative.

Słowa kluczowe

EN

higher carbon sugars; anti-Kishi osmylation; Brimacombe methodology

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 4
• Strony: 521--527
• Opis fizyczny: Bibliogr. 11 poz., rys.

Twórcy

autor

Jarosz S.

autor

Osuch A.

autor

Luboradzki R.

• Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland,

Bibliografia

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