19341-57-2Relevant articles and documents
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Murray,Atkinson
, p. 4023,4024,4025,4026,4027 (1968)
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Synthesis ofnucleoside 3'-thiophosphates in one step procedure
Szczepanik, Maciej B.,Desaubry, Laurent,Johnson, Roger A.
, p. 951 - 953 (1999)
A mild and efficient one-step method of thiophosphorylation was devised for acid-sensitive nucleosides. The procedure is based on thiophosphorylation of nucleoside magnesium alkoxide by 2-chloro-2-thio-l,3,2-dioxaphospholane. The utility and efficiency of this method combined with deprotection of the resulting cyclic triester were demonstrated by its application to the synthesis of both adenosine 3'- and 5'thiophosphates. The procedure does not require protection of the exocyclic amino group and can be successfully used for the thiophosphorylation of nucleosides that are unusually sensitive to depurination. Copyright 1999 by Marcel Dekker, Inc.
Polymer-bound oxathiaphospholane: A solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates
Ahmadibeni, Yousef,Parang, Keykavous
, p. 1955 - 1958 (2007/10/03)
(Chemical Equation Presented) Two polymers bound to N,N-diisopropylamino-1, 3,2-oxathiaphospholane were reacted with unprotected carbohydrates and nucleosides in the presence of 1H-tetrazole, followed by oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent. The 1,3,2-oxathiaphospholane ring-opening with 3-hydroxypropionitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothiophosphate derivatives, respectively, through the elimination of polymer-bound ethylene episulfide. Reactions using this strategy offer the advantages of high regioselectivity, monosubstitution, and facile isolation and recovery of products.