Partial Protection of Carbohydrate Derivatives. Part 23.<sup>1</sup>Simple, Efficient Procedure for the Preparation of 3′- and 2′-0-(Tetrahydropyran-2-YL)Ribonucleoside Derivatives Involving Highly Regioselective 2′,5′-DI-O-Acylation or that Followed by Acyl Migration on Silica Gel and Subsequent O-(Tetrahydropyran-2-YL)Ation
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説明
Abstract Acylation of ribonucleosides with an acyl chloride (1.2–1.5 and 2.2–3.0 mol. equiv. toward the D-ribofuranosyl moiety) in pyridine was induced with high regioselectivity to give the corresponding 2′-acylates and 2′,5′-diacylates, respectively, which were effectively converted into the corresponding 3′-acylates and 3′,5′-diacylates, respectively, by passage down a column of silica gel, followed by crystallization from a solvent. All of the 2′,5′- and 3′,5′-diacylates thus obtained were converted to the corresponding 3′- and 2′-0-(tetrahydropyran-2-yl) derivatives by the usual manner, i.e., (tetrahydropyran-2-yl)ation and subsequent O-deacylation.
収録刊行物
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- Nucleosides and Nucleotides
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Nucleosides and Nucleotides 6 699-736, 1987-09-01
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