Diastereoselective synthesis of 2'-deoxy and 2'-O-methyl dinucleoside (3',5')-methylphosphonates via alkoxymagnesium chloride-mediated nucleoside coupling

Article abstract of DOI:10.1080/07328319708001359

A diastereoselective dinucleoside methylphosphonate synthetic method that features coupling of diastereomerically pure 1,1,1,3,3,3-hexafluoro-2- propyl nucleoside-3'-O-methylphosphonate monomers with 3'-O-protected nucleoside monomers mediated by alkoxymagnesium chloride reagents is described. This synthetic method was found to be diastereospecific in the synthesis of selected 2'-deoxy dinucleoside methyphosphonates and diastereoselective in the synthesis of all sixteen 2'-O-methyl dinucleoside methylphosphonates.

Full text of DOI:10.1080/07328319708001359

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Nucleosides and Nucleotides
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Diastereoselective Synthesis of 2′-
Deoxy and 2′-O-Methyl Dinucleoside
(3′ 5′)-Methylphosphonates via
Alkoxymagnesium Chloride-Mediated
Nucleoside Coupling
William J. Daily a , David A. Schwartz b , Timothy A. Riley b ,
Lyle J. Arnold Jr. b , William B. Marvin a , Michael A. Scurria a ,
Stephanie A. Hopkins a , Michael B. Atkins a , Christine D. Garcia
a & Michael C. Pirrung c
a JBL Scientific Inc. , 277 Granada Dr., San Luis Obispo, CA,
93401
b Genta Inc. , 3550 General Atomics Ct., San Diego, CA, 92121
c Dept. of Chemistry , Duke University , Durham, NC, 27708
Published online: 21 Aug 2006.
To cite this article: William J. Daily , David A. Schwartz , Timothy A. Riley , Lyle J. Arnold Jr. ,
William B. Marvin , Michael A. Scurria , Stephanie A. Hopkins , Michael B. Atkins , Christine D.
Garcia & Michael C. Pirrung (1997) Diastereoselective Synthesis of 2′-Deoxy and 2′-O-Methyl
Dinucleoside (3′ 5′)-Methylphosphonates via Alkoxymagnesium Chloride-Mediated Nucleoside
Coupling, Nucleosides and Nucleotides, 16:4, 417-432, DOI: 10.1080/07328319708001359
To link to this article: http://dx.doi.org/10.1080/07328319708001359
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