A,B-unsaturated sugar D-lactones : Preparation and conjugate addition of hydroxylamines and hydrazines

• Autorzy: Panfil I. , Mostowicz D. , Chmielewski M.
• Języki publikacji: EN

Abstrakty

EN

Oxidation of 2,3-unsaturated glycosides with hydrogen peroxide in the presence of molybdenum trioxide as catalyst provides corresponding A, B-unsaturated sugar d-lactones via the anomeric hydroperoxide stage. Conjugate addition of N-substituted hydroxylamines and hydrazines to these d-enealdonolactones proceeds anti to the C-6 carbon atom. The adducts undergo rearrangement consisting in opening of the lactone ring and formation of 3-substitued isoxazolidin-5-one or 5-substitued pyrazolidin-3-one, respectively. Introduction of a leaving group to the polyol side chain of both heterocycles induces further rearrangements.

Słowa kluczowe

EN

conjugate addition; hydroxylamines; hydrazines; isoxazolidin-5-ones; pyrazolidin-3-ones

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 1999
• Tom: vol. 73 nr 7
• Strony: 1099--1110

Twórcy

autor

Panfil I.

autor

Mostowicz D.

autor

Chmielewski M.

• Instytut Chemii Organicznej PAN 01-224 Warszawa