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Regioselectivity of rhodium nitrene insertion. Syntheses of protected glycals of l-daunosamine, d-saccharosamine, and l-ristosamine. 2005

Kathlyn A Parker, and Wonsuk Chang
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc sunysb.edu

[reaction: see text] The carbamate-protected glycals of naturally occurring 3,4-cis-3-amino-2,3,6-trideoxyhexoses (l-daunosamine, d-saccharosamine, and l-ristosamine) were prepared from noncarbohydrate starting materials. The short, high-yield syntheses are based on the chemoselective insertion of a rhodium nitrene in an allylic C-H bond rather than in a C-H bond that is alpha to an oxygen substituent.

UI MeSH Term Description Entries
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006595 Hexosamines AMINO SUGARS created by adding an amine group to a hexose sugar. Hexosamine
D012238 Rhodium A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh. Rhodium-103,Rhodium 103
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D017672 Nitrogen Compounds Inorganic compounds that contain nitrogen as an integral part of the molecule. Compounds, Nitrogen

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