Synthesis of 5‐methylmercaptopyrimidine nucleosides

The synthesis of a series of new nucleosides, including ribo-, 2′-deoxyribo- and arabinofuranosides of 5-(S-methyl)mercapto-substituted uracil, 4-thiouracil, and cytosine is described. The synthetic methods employed include condensation reactions of the silylated pyrimidine with blocked sugar halides, as well as transformations of both the base and sugar moieties. The separated α and β anomers were identified by nmr spectra as well as by unambiguous synthetic routes or interconversions.

[1]  K. Chadha,et al.  Differential Effects of 5-Methylmercapto-2′-Deoxyuridine on the Replication of Herpes Simplex Virus Type 1 in Two Cell Systems , 1976, Antimicrobial Agents and Chemotherapy.

[2]  C. P. Glaudemans,et al.  The anomers of p-nitrophenyl 2,3,5-tri-O-benzyl-D-arabinofuranoside. , 1976, Carbohydrate research.

[3]  J. Aradi,et al.  BIOCHEMICAL PROPERTIES OF 5‐SULFUR‐SUBSTITUTED PYRIMIDINE NUCLEOSIDES AND NUCLEOTIDES * , 1975, Annals of the New York Academy of Sciences.

[4]  G. Shaw,et al.  Purines, pyrimidines, and imidazoles. Part XXXIII. Synthesis of 5-methylsulphonyluridine and its 5′-mono- and pyro-phosphates , 1970 .

[5]  C. Szántay,et al.  Synthesis of 5-S-substituted 2'-deoxyuridines. Study of the factors influencing stereoselectivity of the silyl modification of the Hilbert-Johnson reaction. , 1969, The Journal of organic chemistry.

[6]  J. Stevens,et al.  The proton magnetic resonance spectra of pentofuranose derivatives. , 1968, The Journal of organic chemistry.

[7]  R. K. Robins,et al.  The synthesis of some quinazoline nucleosides. , 1968, The Journal of organic chemistry.

[8]  Shen Ty,et al.  Nucleosides. V. 2-thiopyrimidine - d -arabinofuranosides. , 1967 .

[9]  L. H. Brown,et al.  A simplified synthesis of 1-beta-d-arabinofuranosyl-5-fluorouracil. , 1966, The Journal of organic chemistry.

[10]  A. Hampton,et al.  Nucleotides. V. Purine ribonucleoside 2',3'-cyclic carbonates. Preparation and use for the synthesis of 5'-monosubstituted nucleosides. , 1966, Biochemistry.

[11]  F. Keller,et al.  A convenient synthesis of 1-beta-D-arabinofuranosylthymine. , 1966, The Journal of organic chemistry.

[12]  J. Fox,et al.  Nucleosides. XXIX. 1-beta-D-arabinofuranosyl-5-fluorocytosine and related arabino nucleosides. , 1966, Journal of medicinal chemistry.

[13]  H. Lewis,et al.  NUCLEOSIDES. I. A NEW SYNTHESIS OF 1-BETA-D-ARABINOFURANOSYL PYRIMIDINE NUCLEOSIDES. , 1965, The Journal of organic chemistry.

[14]  C. Glaudemans,et al.  Syntheses with Partially Benzylated Sugars. III.1 A Simple Pathway to a “cis- Nucleoside,” 9-β-D-Arabinofuranosyladenine (Spongoadenosine) , 1963 .

[15]  M. L. Eidinoff,et al.  Thiation of Nucleosides. II. Synthesis of 5-Methyl-2'-deoxycytidine and Related Pyrimidine Nucleosides1 , 1959 .