Stereoselective Synthesis Of Ribonucleoside 3’,5’-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates

H. C.P.F. Roelen; E. D. Vroom; G. A.V. Der Marel; J. H.van Boom; A. H.J. Wang

doi:10.1080/07328319208021157

Stereoselective Synthesis Of Ribonucleoside 3’,5’-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates

H. C.P.F. Roelen, E. D. Vroom, G. A.V. Der Marel, J. H.van Boom, A. H.J. Wang

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

Monophosphonylation of 2’-protected ribonucleosides (i.e., 2’-O-THP-uridine and 2’-O-THP-N6-levulinoyl-adenosine) with the bifunctional reagents bis[( 6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole gave the chirally pure ‘,5’methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis. the corresponding pure Sp-diastereoisomers.

Original language	English
Pages (from-to)	141-156
Number of pages	16
Journal	Nucleosides and Nucleotides
Volume	11
Issue number	1
DOIs	https://doi.org/10.1080/07328319208021157
Publication status	Published - Jan 1 1992
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Genetics

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@article{0b3035edd58748d49d9bfe889bd9f241,

title = "Stereoselective Synthesis Of Ribonucleoside 3{\textquoteright},5{\textquoteright}-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates",

abstract = "Monophosphonylation of 2{\textquoteright}-protected ribonucleosides (i.e., 2{\textquoteright}-O-THP-uridine and 2{\textquoteright}-O-THP-N6-levulinoyl-adenosine) with the bifunctional reagents bis[( 6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole gave the chirally pure {\textquoteleft},5{\textquoteright}methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis. the corresponding pure Sp-diastereoisomers.",

author = "Roelen, {H. C.P.F.} and Vroom, {E. D.} and {Der Marel}, {G. A.V.} and Boom, {J. H.van} and Wang, {A. H.J.}",

note = "Funding Information: One of us, H.C.P.F. Roelen thanks the Netherlands Organization for Scientific Research (NWO) for financial support. Further we greatly acknowledge Mr. P.J.M. Van Haastert for the determination of chemotaxicity of the CAMP derivatives.",

year = "1992",

month = jan,

day = "1",

doi = "10.1080/07328319208021157",

language = "English",

volume = "11",

pages = "141--156",

journal = "Nucleosides and Nucleotides",

issn = "0732-8311",

publisher = "Taylor and Francis Ltd.",

number = "1",

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T1 - Stereoselective Synthesis Of Ribonucleoside 3’,5’-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates

AU - Roelen, H. C.P.F.

AU - Vroom, E. D.

AU - Der Marel, G. A.V.

AU - Boom, J. H.van

AU - Wang, A. H.J.

N1 - Funding Information: One of us, H.C.P.F. Roelen thanks the Netherlands Organization for Scientific Research (NWO) for financial support. Further we greatly acknowledge Mr. P.J.M. Van Haastert for the determination of chemotaxicity of the CAMP derivatives.

PY - 1992/1/1

Y1 - 1992/1/1

N2 - Monophosphonylation of 2’-protected ribonucleosides (i.e., 2’-O-THP-uridine and 2’-O-THP-N6-levulinoyl-adenosine) with the bifunctional reagents bis[( 6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole gave the chirally pure ‘,5’methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis. the corresponding pure Sp-diastereoisomers.

AB - Monophosphonylation of 2’-protected ribonucleosides (i.e., 2’-O-THP-uridine and 2’-O-THP-N6-levulinoyl-adenosine) with the bifunctional reagents bis[( 6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole gave the chirally pure ‘,5’methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis. the corresponding pure Sp-diastereoisomers.

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Stereoselective Synthesis Of Ribonucleoside 3’,5’-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates

Abstract

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