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Stereoselective synthesis of 1'-C-carbon-subsituted 4'-thionucleosides from 4-thiofuranoid glycal. 2001

K Haraguchi, and H Takahashi, and H Tanaka
School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142-8555, Japan.

PhSeCl or NIS-initiated glycosylation to 2-5, which were prepared through lithiation of 4-thiofuranoid glycal 1, proceeded stereoselectively to give the target 1'-C-carbon-substituted 4'-thiopyrimidine nucleosides. This synthetic method enabled us to synthesize 4'-thioanalogue 13 of nucleoside antibiotic angustmycin.

UI MeSH Term Description Entries
D006031 Glycosylation The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION). Protein Glycosylation,Glycosylation, Protein
D012833 Siloxanes Silicon polymers that contain alternate silicon and oxygen atoms in linear or cyclic molecular structures. Polysiloxane,Polysiloxanes,Siloxane
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
D013876 Thiophenes A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur. Thiophene

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