By E. Merck. Authorized translation by Henry Schenck ...
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All five natural ribonucleosides were described with a 3’-C-trifluoromethyl group, following a synthesis involving D-xylose as starting material <95NN185; 03NNNA2195>. Their 3’-deoxy version was published by Sharma, and involved a Barton deoxygenation to remove the 3’-hydroxyl group <00NNNA757>. 4 Modifications at C-4’ Modifications at the 4’ position of ribo- and deoxyribonucleosides have drawn attention in the past few years due to several reports of anti-HIV activity and, more recently, anti-HCV activity.
C. -J. Liu, Z. Yang, H. J. F. K. -K. Hwang, M. G. Nantermet, J. Am. Chem. Soc. 1995, 117, 634. 95JACS7904 C. Bisang, C. Weber, J. A. F. van Gunsteren, I. R. A. Robinson, J. Am. Chem. Soc. 1995, 117, 7904. H. -G. N. Anjeh, N. L. Horst, T. Kobayashi, T. Okano, N. Tsugawa, J. Org. Chem. 1995, 60, 1617. H. Posner, K. Afarinkia, H. Dai, Org. Synth. 1995, 73, 231. 95TL5939 H. Okamura, T. Iwagawa, M. Nakatani, Tetrahedron Lett. 1995, 35, 5939. D. Winkler, Chem. Rev. 1996, 96, 167. D. S. Liebeskind, J.
A third approach published consisted of building a carbocycle from D-ribose, and condensing the 39 Recent developments in the chemistry of nucleosides chloropurine base via a Mitsunobu coupling <04JOC3993>. Yang also described the synthesis of 5’-homoneplanocin <05JMC5043> and the synthesis of (-)-3-deazaaristeromycin <04TL8981> through a similar route. A new chiral synthesis of 6’-β-fluoroaristeromycin was described using cis-4-acetoxy-2-cyclopentene-1-ol as starting material <05TL7535>. Enzymatic resolution of (±)-1-acetoxy-4-(nitromethyl)-2-cyclopentene provided the desired starting material for the synthesis of carbanucleosides and 5’-nor-1’-homo carbanucleosides <02T9889>.