15981-92-7Relevant articles and documents
The Reaction of 2′-Deoxynucleosides with N-(2-Chloro1,1,2-trifluoroethyl)diethylamine: Mechanisms of O2,3′-Anhydro-2′-deoxynucleoside and By-product Formation
Sehgal, Raj K.,Turcotte, Joseph G.
, p. 24 - 25 (1998)
Reaction mechanisms consistent with the formation of isopropylidene-like trans-furanose-3′,5′-[2-(R)(S)-aminochlorofluoromethyl-1,3-dioxanyl] -2′-deoxynucleoside intermediates 6, O2,3′-anhydro-2′-deoxynucleosides 7 and other minor reaction products and the yield-limiting effect of 6 on the cyclization of 7 are proposed.
A Novel One-step Procedure for the Conversion of Thymidine into 2,3'-Anhydrothymidine
Rao, T. Sudhakar,Reese, Colin B.
, p. 997 - 998 (1989)
2,3'-Anhydrothymidine (3) is obtained in ca. 65percent yield by heating thymidine (2) with an excess of diphenyl sulphite in dimethylacetamide solution; (3) reacts with lithium azide to give 3'-azido-3'-deoxythymidine in good yield.
Radiosynthesis of [18F]-labelled pro-nucleotides (ProtIDes)
Cavaliere, Alessandra,Probst, Katrin C.,Paisey, Stephen J.,Marshall, Christopher,Dheere, Abdul K.H.,Aigbirhio, Franklin,McGuigan, Christopher,Westwell, Andrew D.
, (2020/02/18)
Phosphoramidate pro-nucleotides (ProTides) have revolutionized the field of anti-viral and anti-cancer nucleoside therapy, overcoming the major limitations of nucleoside therapies and achieving clinical and commercial success. Despite the translation of P
Antiviral activity of 2,3′-anhydro and related pyrimidine nucleosides against hepatitis B virus
Srivastav, Naveen C.,Mak, Michelle,Agrawal, Babita,Tyrrell, D. Lorne J.,Kumar, Rakesh
scheme or table, p. 6790 - 6793 (2011/01/04)
Various 2,3′-anhydro analogs of 5-substituted 1-(2-deoxy-β-d- lyxofuranosyl)uracils (10-15) and a related 1-(3-O-mesyl-2-deoxy-β-d- lyxofuranosyl) pyrimidine nucleoside analog (18) have been synthesized for evaluation as a new class of potential anti-HBV
Synthesis, structure, and biological evaluation of C-2 sulfonamido pyrimidine nucleosides
Krizmani?, Irena,Vi?njevac, Aleksandar,Lui?, Marija,Glava?-Obrovac, Ljubica,?ini?, Mladen,?ini?, Biserka
, p. 4047 - 4057 (2007/10/03)
The C-2 sulfonamido pyrimidine nucleosides were prepared by opening the 2,2′- or 2,3′-bond in anhydronucleosides under nucleophilic attack of sulfonamide anions. Reaction of the sodium salt of p-toluenesulfonamide or 2-(aminosulfonyl)-N,N-dimethylnicotinamide with 2,2′-anhydro-1-(β-D-arabinofuranosyl)cytosine gave the C-2 sulfonamido derivatives in excellent yields. Ring opening of the less reactive 2,2′-anhydrouridine and 2,3′-anhydrothymidine could be accomplished with DBU/CH3CN activation of p-toluenesulfonamide, giving moderate yields for C-2 sulfonamido derivatives. The action of acetic acid or ZnBr2/CH2Cl2 on 5-methyl-N2-tosyl-1-(2-deoxy-5-O-trityl-β-D-threo- pentofuranosyl)isocytosine led to the cleavage of both the protection group and the nucleoside bond, yielding 5-methyl-N2-tosylisocytosine as the major product. Structures of the prepared C-2 sulfonamido nucleosides were confirmed by the 1D and 2D NMR experiments, and X-ray structural analysis of 4-imino-N2-tosylamino-1-(β-D-arabinofuranosyl)pyrimidine. Both methods confirmed β-configuration and anti-conformation of the 2-sulfonamido nucleosides. The investigated compounds displayed moderate inhibition of tumor cell growth in vitro, as determined by the MTT assay using six different human tumor cell lines.
An improved synthesis of azidothymidine
Balagopala, Meher I.,Ollapally, Abraham P.,Lee, Henry J.
, p. 899 - 906 (2007/10/03)
A convenient and high yielding procedure is described for a direct conversion of thymidine (1) into 2,3'-anhydrothymidine (2) using the Mitsunobu reaction. Isolation and characterization of two new compounds, 3 and 4, are discussed. AZT has been synthesized from 1 in two steps, in 62% overall yield, by heating 2 with NaN3 in DMF.
Synthesis of 2,3'-anhydro-2'-deoxyuridines and 2,3'-didehydro-2',3'-dideoxyuridines using polymer supported fluoride
Larsen,Kofoed,Pedersen
, p. 1121 - 1125 (2007/10/02)
Reaction of methyl 5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-α,β-D-eryt hro-pentofuranoside (2) with silylated uracils 3 using trimethylsilyl trifluoromethanesulfonate (TMS triflate) as catalyst afforded after crystallization in Et2O the corresponding β-nucleosides 4. Reaction of 4 with tetrabutylammonium fluoride (TBAF) or Amberlyst A-26 resin (F--form) in THF at room temperature or at reflux gave the corresponding deprotected 2,3'-anhydro-2'-deoxyuridines 6 and 2',3'-didehydro-2',3'-dideoxyuridines 7, respectively.
Action of nucleophiles on 2,3'-anhydrothymidine: Side-reactions involving the possible intermediacy of 2,5'-anhydro-1-(2-deoxy-β-D-threo-pentofuranosyl)thymine
Joshi,Reese
, p. 2371 - 2374 (2007/10/02)
2,3'-Anhydrothymidine (1) reacts with the sodium salt of propane-2-thiol and with sodium phenyl selenide to give 5'-substituted products [(3b) and (3c), respectively] in addition to the expected 3'-substituted 2',3'-dideoxynucleoside derivatives [(2b) and
Conversion of Some Pyrimidine 2'-Deoxyribonucleosides into the Corresponding 2',3'-Didehydro-2',3'-dideoxynucleosides
Joshi, Bhalchandra V.,Rao, T. Sudhakar,Reese, Colin B.
, p. 2537 - 2544 (2007/10/02)
Thymidine 4b was converted into 2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 7b in ca. 65percent isolated yield by being heated at 155 deg C with an excess of diphenyl sulfite and 1-methylimidazole in N,N-dimethylacetamide solution. 2'-Deoxyuridine 4a, 2'-deoxy-5-ethyluridine 4c and 2'-deoxy-5-fluorouridine 4d were similarly converted into 2,3'-anhydronucleosides which were isolated as their 5'-O-(tert-butyldimethylsilyl) derivatives 8a, 8c and 8d in 51, 50 and 59percent yield, respectively.When the oxetane derivatives 5a-d, prepared by the literature procedure from the parent 2'-deoxynucleosides 4a-d, were heated with an excess of sodium hydride in N,N-dimethylacetamide solution at 100 deg C, they were converted into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6a-d in 68, 76, 69 and 74percent isolated yield, respectively.The latter compounds were similarly prepared from the 2,3'-anhydronucleosides 7a-d in 71, 81, 69 and 74percent isolated yield, respectively. 2,3'-Anhydro-5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-(trifluoromethyl)- and -5-iodo-1-(β-D-threo-pentofuranosyl)uracil 8e and 8f, which were themselves prepared from the parent 2'-deoxynucleosides 4e and 4f, respectively, in ca. 60 and 50percent yield, were converted by a three-step procedure via the intermediate 2'-deoxy-3'-(phenylseleno) derivatives 10e and 10f into the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides 6e and 6f in 52 and 49percent overall yield, respectively.Compound 8e was also converted into 2',3'-dideoxy-5-(trifluoromethyl)uridine 11b and 3'-azido-2',3'-dideoxy-5-(trifluoromethyl)uridine 11c in 49 and 66percent overall yield, respectively.
New synthetic 'tricks'. Trimethylsilyl triflate mediated cleavage of hindered silyl ethers
Bou,Vilarrasa
, p. 567 - 568 (2007/10/02)
An alternative, mild procedure for the cleavage of t-butyldimethylsilyl and triphenylsilyl ethers to alcohols is shown, which is based on an exchange reaction with trimethylsilyl triflate below 0°C. t-Butyldiphenylsilyl groups are not removed under these
