Highly efficient synthesis of 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′,3′-trans-elimination. From iodomethylcyclopropanes to thiirane analogs

[1]  A. Mota,et al.  Highly β-stereoselective nucleosidation from α-d-xylo- and α-d-ribo-furanose 1,2-thiocarbonates , 2004 .

[2]  A. Mota,et al.  Efficient and selective synthesis of glycofuranosyl azides and nucleosides from cyclic 1,2-thiocarbonate sugars. , 2003, Organic letters.

[3]  C. Len,et al.  Synthesis of acyclic bis-vinyl pyrimidines: a general route to d4T via metathesis , 2003 .

[4]  P. Herdewijn,et al.  Straightforward Synthesis of Labeled and Unlabeled Pyrimidine d4Ns via 2′,3′‐Diyne seco Analogues through Olefin Metathesis Reactions , 2003 .

[5]  M. Kiso,et al.  AN EFFICIENT AND STRAIGHTFORWARD SYNTHESIS OF SIALYL Le X GLYCOLIPID AS A POTENT SELECTIN BLOCKER[[1]] , 2002 .

[6]  R. Field,et al.  Iodine and its interhalogen compounds: versatile reagents in carbohydrate chemistry. XIV. Glycosylated amino acid synthesis , 2001 .

[7]  Bang-Chi Chen,et al.  A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates , 1998 .

[8]  I. Izquierdo,et al.  An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2=diols , 1997 .

[9]  I. I. Cubero,et al.  Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters , 1997 .

[10]  S. P. Brundidge,et al.  5′-Benzoyl-2′α-bromo-3′-O-methanesulfonylthymidine: A superior nucleoside for the synthesis of the anti-AIDS drug D4T (Stavudine) , 1995 .

[11]  J. H. Boom,et al.  Synthesis of a Methyl Heptaglucoside with Phytoalexin Elicitor Activity Based on Oxidative Coupling of Glucals , 1995 .

[12]  K. Osumi,et al.  Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases , 1994 .

[13]  F. A. Luzzio,et al.  A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine) , 1994 .

[14]  Carlos Jaramillo,et al.  An Ezomycin Model Glycosylation , 1994 .

[15]  K. Osumi,et al.  Stereoselective Synthesis of 1,2-cis-N-Glycosides by the N-Bromosuccinimide Promoted Reaction of Thioglycosides with Silylated Pyrimidme Bases , 1993 .

[16]  D. Huryn,et al.  AIDS-driven nucleoside chemistry. , 1992 .

[17]  C. Kim,et al.  Facile, highly stereoselective synthesis of 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3t'-dideoxy nucleosides via a furanoid glycal intermediate , 1992 .

[18]  M. Tozer,et al.  The iodination and iodocyclisation of some alkenylmalonates , 1992 .

[19]  S. Eguchi,et al.  Synthesis of 2,2'-anhydro-1-(3'-deoxy-3'-iodo-β-D-arabino-furanosyl)thymine and its derivatives as versatile synthetic intermediates , 1992 .

[20]  E. Pedersen,et al.  2,3-Dideoxy-furanoses in Convergent Syntheses of 2′,3′-Dideoxy Nucleosides , 1992 .

[21]  S. Knapp,et al.  Nucleoside synthesis from thioglycosides , 1991 .

[22]  H. Kawakami,et al.  Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides Utilizing Coupling Reactions Between Nucleic Bases and Phenylthio-Substituted 2, 3-Dideoxyribose. , 1991 .

[23]  H. Mitsuya,et al.  Molecular targets for AIDS therapy. , 1990, Science.

[24]  E. Clercq,et al.  Design of Anti-AIDS Drugs , 1990 .

[25]  J. C. Martin,et al.  Comparison of in vitro biological properties and mouse toxicities of three thymidine analogs active against human immunodeficiency virus , 1990, Antimicrobial Agents and Chemotherapy.

[26]  J. Starrett,et al.  Preparation of 1-(2,3-dideoxy-.beta.-D-glycero-pent-2-enofuranosyl)thymine (d4T) and 2',3'-dideoxyadenosine (ddA): general methods for the synthesis of 2',3'-olefinic and 2',3'-dideoxy nucleoside analogs active against HIV , 1989 .

[27]  P. Roey,et al.  General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides , 1989 .

[28]  J. Starrett,et al.  1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent. , 1989, Journal of medicinal chemistry.

[29]  H. Pachéco,et al.  Synthèse de nucléosides pyrimidiques non protégés en O-2′ à partir de sulfites cycliques en C-1—C-2 , 1988 .

[30]  R. Schinazi,et al.  Potent and selective in vitro activity of 3'-deoxythymidin-2'-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus. , 1987, Biochemical pharmacology.

[31]  E. De Clercq,et al.  3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents. , 1987, Journal of medicinal chemistry.

[32]  E. De Clercq,et al.  The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2',3'-didehydro-2',3'-dideoxyribonucleosides: a comparison with their parental 2',3'-dideoxyribonucleosides. , 1987, Molecular pharmacology.

[33]  T. Matsui,et al.  Inhibitory effect of 2',3'-didehydro-2',3'-dideoxynucleosides on infectivity, cytopathic effects, and replication of human immunodeficiency virus , 1987, Antimicrobial Agents and Chemotherapy.

[34]  E. Gelmann,et al.  ADMINISTRATION OF 3'-AZIDO-3'-DEOXYTHYMIDINE, AN INHIBITOR OF HTLV-III/LAV REPLICATION, TO PATIENTS WITH AIDS OR AIDS-RELATED COMPLEX , 1986, The Lancet.

[35]  Y. Mizuno.  The organic chemistry of nucleic acids , 1986 .

[36]  F. Hansske,et al.  A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2′-ene and 2t',3′-dideoxynucleosides☆ , 1984 .

[37]  B. Samuelsson,et al.  A FACILE PREPARATION OF 2′,3′-UNSATURATED NUCLEOSIDES AND HEXOPYRANOSIDES FROM ACETYLATED HALOHYDRINS BY REDUCTIVE ELIMINATION , 1982 .

[38]  Manfred E. Wolff,et al.  Burger's Medicinal chemistry , 1980 .

[39]  J. G. Moffatt,et al.  Reactions of 2-Acyloxyisobutyryl Halides with Nucleosides. 1V.l A Facile Synthesis of 2,3-Unsaturated Nucleosides Using Chromous Acetate , 1974 .

[40]  J. G. Moffatt,et al.  Reactions of 2-acyloxyisobutyryl halides with nucleosides. II. Reactions of adenosine. , 1973, Journal of the American Chemical Society.

[41]  J. G. Moffatt,et al.  Reactions of 2-acyloxyisobutyryl halides with nucleosides. I. Reactions of model diols and of uridine. , 1973, Journal of the American Chemical Society.

[42]  J. G. Moffatt,et al.  Halo sugar nucleosides. 3. Reactions for the chlorination and bromination of nucleoside hydroxyl groups. , 1972, The Journal of organic chemistry.

[43]  J. Chua,et al.  Nucleosides. IX. The formation of 2',2'-unsaturated pyrimidine nucleosides via a novel beta-elimination reaction. , 1966, The Journal of organic chemistry.

[44]  J. Horwitz,et al.  Nucleosides. VI. The Introduction of Unsaturation into the Carbohydrate of a Pyrimidine Nucleoside via a 2,3′-Anhydro Bond , 1964 .

[45]  G. Crank,et al.  Derivatives of orthoacids. II. The preparation of olefins from 1,2-diols , 1964 .