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Ramamurty C.V.S.,Natural Products and Glycotechnology Research Institute Inc. | Ganney P.,Natural Products and Glycotechnology Research Institute Inc. | Rao C.S.,CiVentiChem | Fraser-Reid B.,Natural Products and Glycotechnology Research Institute Inc.
Journal of Organic Chemistry | Year: 2011

The 3,5-di-O-benzoyl n-pentenyl orthoesters of the four pentofuranoses have been prepared. The first key intermediate in each case is the methyl pentofuranoside(s), and a user-friendly procedure for the preparation of each, based on the Callam-Lowary precedent, is described, whereby formation of the crucial α/β anomeric mixture is optimized. The mixture is used directly to prepare the corresponding perbenzoylated pentofuranosyl bromide(s) and then the title compounds. © 2011 American Chemical Society. Source


Fraser-Reid B.,Natural Products and Glycotechnology Research Institute Inc. | Ganney P.,Natural Products and Glycotechnology Research Institute Inc. | Ramamurty C.V.S.,Natural Products and Glycotechnology Research Institute Inc. | Gomez A.M.,Institute Quimica Organica General IQOG CSIC | Lopez J.C.,Institute Quimica Organica General IQOG CSIC
Chemical Communications | Year: 2013

Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as -78°C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized. © 2013 The Royal Society of Chemistry. Source

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