- Synthesis of novel Pyridine-, Pyrindine- and Isoquinoline-substituted α- and β-C-nucleosides of 2-deoxy-D-ribose
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The novel imido esters of 2-deoxy-α- and -β-D-ribose 8 and 9 have been synthesized and successfully transformed to the protected 1,2,4-triazine-C-nucleosides 11 and 12 using an inverse type Diels-Alder reaction with the 1,2,4,5-tetrazine 10. The electron deficient diazadiene system of both C-nucleosides 11 and 12 proved to be highly reactive in a consecutive [4 + 2] cycloaddition with inverse electron demand towards several electron rich dienophiles yielding after successful deprotection the novel pyridine-, pyrindine- and isoquinoline-C-nucleosides 15, 18 and 21 of 2-deoxy-α-D-ribose and 23, 25 and 27 of 2-deoxy-β-D-ribose.
- Seitz, Gunther,Lachmann, Jens
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p. 549 - 558
(2007/10/03)
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- Stereoselective β-C- and β-S-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protective Group
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β-C-2-Deoxyribofuranosides and β-S-2-deoxyribofuranosides are prepared stereoselectively from 1-O-acetyl-5-O-benzyl-3-O--2-deoxy-D-erythro-pentofuranose or the corresponding 3-O-(2-pyridylmethyl)pentofuranose N-oxide by the reacti
- Ichikawa, Yuh-ichiro,Kubota, Hideki,Fujita, Ken'ichi,Okauchi, Tatsuo,Narasaka, Koichi
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p. 845 - 852
(2007/10/02)
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- STEREOCHEMICAL CONTROL AS A FUNCTION OF PROTECTING-GROUP PARTICIPATION IN 2-DEOXY-D-ERYTHRO-PENTOFURANOSYL NUCLEOSIDES
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Possible features controlling the anomeric ratios in the synthesis of the antiviral antibiotic dihydro-5-azathymidine have been examined.Replacement of the 3- and 5-(4-methylbenzoyl) protecting groups in 2-deoxy-D-erythro-pentofuranosyl chloride by benzyl
- Wierenga, Wendell,Skulnick, Harvey I.
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