Pathak, T. ; Chattopadhyaya, J. (1987) A regio and stereoselective synthesis of 2',2',3',4'-tetradeuterio-2'-deoxy nucleosides Tetrahedron, 43 (18). pp. 4227-4234. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)83465-7
Abstract
Methyl β-D-arabinopyranoside (1) has been stereoselectively deuterated, by the treatment of deuterated Raney N1 in D2O, to give the 2,3,4-trideutereo-βD-arabinopyranoside 2 in 33% yield. It was then converted to 3,4-isopropylidene derivative 3b in 90% yield and subsequently derivatized to 2-0-phenylthiocarbonate 4 (85%). Compound 4 was deoxygenated at C-2 and was isolated as 2:8 (α:β) anomeric mixture 6 in 70% yield (based on 4 in two steps). Compound 6 was converted to the free sugar 7, by the treatment of 0.8 M aqueous HCl, which was then successively converted to pentofuranosides: 8 → 9 → 10; the crystalline α-chlorosugar 10 was thus obtained 1n 60% yield in four steps starting from 6. Subsequently α-chlorosugar 10 was coupled to different nucleobases of DNA to give 2',2',3',4'-tetradeuterio-2'-deoxynucleosides in moderate yields.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
ID Code: | 104302 |
Deposited On: | 16 Mar 2017 12:11 |
Last Modified: | 16 Mar 2017 12:11 |
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