Total synthesis of 2‐(β‐D‐ribofuranosyl)thiazole‐4‐carboxamide (Tiazofurin) and of precursors of ribo‐C‐nucleosides
- 13 December 1989
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 72 (8) , 1825-1832
- https://doi.org/10.1002/hlca.19890720819
Abstract
(1R,2S,4R)‐2‐Cyano‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐yl (1S′)‐camphanate (5) was transformed into (−)‐methyl 2,5‐anhydro‐3,4,6‐O‐tris[(tert‐butyl)dimethylsilyl]‐D‐allonate (2), (+)‐1,3‐diphenyl‐2‐{2′,3′,5′‐O‐tris[(tert‐butyl)dimethylsilyl]‐β‐D‐ribofuranosyl}imidazolidine (3), and the benzamide 20 of 1‐amino‐2,5‐anhydro‐1‐deoxy‐3,4,6‐O‐tris‐[((tert‐butyl)dimethylsily)]‐D‐allitol. Compound 2 was converted efficiently into optically active tiazofurin (1).This publication has 72 references indexed in Scilit:
- Synthesis of Carbohydrates and Derivatives from 7-Oxanorbornenes ("Naked Sugars")Published by American Chemical Society (ACS) ,1989
- Highly Stereoselective Total Syntheses of 2,5‐Anhydro‐4‐deoxy‐D‐ribo‐hexonic Acid and of (1S)‐1‐C‐(6‐amino‐7H‐purin‐8‐yl)‐1,4‐anhydro‐3‐deoxy‐D‐erythro‐pentitol (= cordycepin C)Helvetica Chimica Acta, 1989
- Total Synthesis of L‐Allose, L‐Talose, and derivatives.Helvetica Chimica Acta, 1989
- Enantiomerically pure 7‐oxabicylo[2.2.1]hept‐5‐en‐zyl derivatives as synthetic intermediates. Part III. Total synthesis of D‐ and L‐ribose derivativesHelvetica Chimica Acta, 1988
- Optical resolution of 7‐oxabicyclo[2.2.1]hept‐21‐ene derivatives. Diastereoselectivity in the formation of cyanohydrine‐brucine complexesHelvetica Chimica Acta, 1984
- THIATION WITH 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4- DITHIADIPHOSPHETANE 2,4-DISULFIDE: N-METHYLTHIOPYRROLIDONEOrganic Syntheses, 1984
- The Preparation of Optically Pure 7‐Oxabicyclo [2.2.1]hept‐2‐ene Derivatives. The CD Spectrum of (+)‐(1R)‐7‐Oxabicyclo [2.2.1]hept‐5‐en‐2‐oneHelvetica Chimica Acta, 1983
- Broad-spectrum antiviral activity of 2-beta-D-ribofuranosylselenazole-4-carboxamide, a new antiviral agentAntimicrobial Agents and Chemotherapy, 1983
- Nucleic acid components and their analogues. CXXIII. Synthesis of homouridine and homocytidineCollection of Czechoslovak Chemical Communications, 1969
- Nucleic acid components and their analogues. CXVIII. Synthesis of 8-β-D-ribofuranosyladenine starting from 2,5-anhydro-D-allonic acidCollection of Czechoslovak Chemical Communications, 1969