Tetrahedron letters

A general approach to nucleoside 3′-and 5′-monophosphates

Y Hayakawa, S Wakabayashi, T Nobori, R Noyori

Index: Hayakawa, Y.; Wakabayashi, S.; Nobori, T.; Noyori, R. Tetrahedron Letters, 1987 , vol. 28, # 20 p. 2259 - 2262

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Citation Number: 41

Abstract

This method, however, is not always satisfactory in the 3′-O-phosphorylation. In our experience, for instance, sequential treatment of 1 (B = Cy;R = TBDMS) with (1) POCl 3 (2 equiv) in PO(OCH 3 ) 3 at 0 °C for 4 h, (2) H 2 O, overnight, and (3) TBAF (excess) in THF at 25 °C for 1.5 h gave 3 (B = Cy) in only 27% yield (HPLC analysis) together with many side-products. ... No enzymatic 3′-O-phosphorylation methods have been reported.