Organotransition metal modified sugars 4. Carbene complex functionalized acyclic carbohydrates

A synthetic strategy based on a combination of sugar electrophiles and transition metal nucleophiles allows the metal carbene functionalization of acyclic carbohydrates. Following this methodology the per- O-acetylated methoxycarbene complexes 8–14 are prepared in moderate to good yields. Upon react...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 548; no. 1; pp. 91 - 98
Main Authors Dötz, K.H., Ehlenz, R., Straub, W., Weber, J.C., Airola, K., Nieger, M.
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 05.12.1997
Elsevier
Subjects
Carbohydrates
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Conformation of carbohydrates
Glycosyl carbene complexes
Optically active carbene complexes
Physical Sciences
Science & Technology
Glycosyl carbene complexes
Carbohydrates
Optically active carbene complexes
Conformation of carbohydrates
carbohydrates
MANGANESE
ACIDS
optically active carbene complexes
ORGANIC SYNTHESES
DIETHYL
conformation of carbohydrates
C-GLYCOSIDES
CONFORMATION
DERIVATIVES
glycosyl carbene complexes
DIPHENYL DITHIOACETALS
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Summary:A synthetic strategy based on a combination of sugar electrophiles and transition metal nucleophiles allows the metal carbene functionalization of acyclic carbohydrates. Following this methodology the per- O-acetylated methoxycarbene complexes 8–14 are prepared in moderate to good yields. Upon reaction with ammonia they undergo aminolysis to give the aminocarbene complexes 16–18. 1H-NMR studies indicate that in solution the d-galacto and l-arabino complexes adopt extended planar zigzag conformations. A similar conformational preference is observed for the solid state as established by X-ray studies on the d-galacto derivatives 8 and 15.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(97)00335-5