Journal
ORGANIC LETTERS
Volume 7, Issue 10, Pages 1955-1958Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol050385w
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- NCRR NIH HHS [P20 RR16457] Funding Source: Medline
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[GRAPHICS] 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-hydroxyproplonitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothlophosphate 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.
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