Various sugars were C-glycosylated by treatment with methylenetriphenyl-phosphorane and subsequent iodocyclization of the resulting hept- and hex-enitols. In all cases, a Cglycofuranosyl compound was obtained, except for 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-d-manno-hept-1-enitol which yielded a C-pyranosyl compound. High stereoselectoin, with formation of the 1,2-cis adduct as major product, was observed when an asymmetric center was present in the position adjacent to the double bond.

Synthesis of C-glycosyl compounds by the wittig iodocyclization procedure. Differences from mercuriocyclization / F. Nicotra, L. Panza, F. Ronchetti, G. Russo, L. Toma. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 171:1(1987), pp. 49-57.

Synthesis of C-glycosyl compounds by the wittig iodocyclization procedure. Differences from mercuriocyclization

F. Ronchetti;G. Russo
Penultimo
;
1987

Abstract

Various sugars were C-glycosylated by treatment with methylenetriphenyl-phosphorane and subsequent iodocyclization of the resulting hept- and hex-enitols. In all cases, a Cglycofuranosyl compound was obtained, except for 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-d-manno-hept-1-enitol which yielded a C-pyranosyl compound. High stereoselectoin, with formation of the 1,2-cis adduct as major product, was observed when an asymmetric center was present in the position adjacent to the double bond.
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/176230
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