Biomaterial Database

Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars. 2009

David Crich, and Sébastien Picard

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr

Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

UI	MeSH Term	Description	Entries
D008360	Mannosephosphates	Phosphoric acid esters of mannose.
D008698	Mesylates	Organic salts or esters of methanesulfonic acid.	Mesilate,Methanesulfonates,Mesilates,Mesylate,Methylenesulfonates
D010880	Piperidines	A family of hexahydropyridines.
D011743	Pyrimidines	A family of 6-membered heterocyclic compounds occurring in nature in a wide variety of forms. They include several nucleic acid constituents (CYTOSINE; THYMINE; and URACIL) and form the basic structure of the barbiturates.
D000644	Quaternary Ammonium Compounds	Derivatives of ammonium compounds, NH4+ Y-, in which all four of the hydrogens bonded to nitrogen have been replaced with hydrocarbyl groups. These are distinguished from IMINES which are RN	Quaternary Ammonium Compound,Ammonium Compound, Quaternary,Ammonium Compounds, Quaternary,Compound, Quaternary Ammonium
D000812	Anhydrides	Chemical compounds derived from acids by the elimination of a molecule of water.	Anhydride
D001597	Benzylidene Compounds	Compounds which include a double-bonded carbon atom that is directly attached to a benzene ring. While this category is named after the highly reactive compound benzylidene, the compounds listed under it occur through a variety of synthetic pathways.	Benzylidene Compound,Benzylidene Derivative,Benzylidene Derivatives,Phenylmethylene Derivative,Phenylmethylene Derivatives,Compound, Benzylidene,Compounds, Benzylidene,Derivative, Benzylidene,Derivative, Phenylmethylene,Derivatives, Benzylidene,Derivatives, Phenylmethylene
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
D013865	Thioglycosides
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