Recherche d'analogues de nucléosides à activité antivirale

Tronchet, J. M. J.; Valero, M. J.

doi:10.1002/hlca.19790620828

Cited by 14 publications

(12 citation statements)

References 16 publications

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“…(s, 5-CH3), 2.07 (s, CHgCO), 2.S-2.7 (m, 2 *), 4.15 (m, CH3CH2), 4.58 (m, H4. ), 5.2 (m, Ha,), 6.07 (d, H6. ), 6.25 (t, Hr), 7.05 (dd, H5•), 7.6 (H6).…”

Section: Methodsmentioning

confidence: 99%

“…Ethyl 3-0-Acetyl-l,2,5,6-tetradeoxy-l-(thymin-l-yl)-/8-Derythro-heptofuranuronate (6). A solution of ethyl 3-Oacetyl-l,2,5,6-tetradeoxy-l-(thymin-l-yl)-/3-D-ri'5o-hept-5-enofuranuronate (3; 245 mg, 0.7 mmol) in MeOH (50 mL) containing Pt02 catalyst (55 mg) was hydrogenated at ambient temperature and 48 psi of H2 for 20 h, filtered, and evaporated to a syrup: yield 237 mg (96%); NMR 1.15 (m, CHgCHü), 1.8 (s, 5-CH3), 1.7-2.1 (m, 2 Hy and 2 *), 2.04 (s, CH3CO), 2.35 (m, 2 H2,), 3.3 (H20), 3.9 (m, H4.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of ethyl 3-Oacetyl-l,2,5,6-tetradeoxy-l-(thymin-l-yl)-/3-D-ri'5o-hept-5-enofuranuronate (3; 245 mg, 0.7 mmol) in MeOH (50 mL) containing Pt02 catalyst (55 mg) was hydrogenated at ambient temperature and 48 psi of H2 for 20 h, filtered, and evaporated to a syrup: yield 237 mg (96%); NMR 1.15 (m, CHgCHü), 1.8 (s, 5-CH3), 1.7-2.1 (m, 2 Hy and 2 *), 2.04 (s, CH3CO), 2.35 (m, 2 H2,), 3.3 (H20), 3.9 (m, H4. ), 4.05 (q, CH3CH2), 5.05 (m, H3<), 6.12 (t, Jv,2, = 6 Hz, Hr), 7.6 (m, He), 12.1 (br, NH); mass spectrum, m/e 229 (sugar), 249 [(M -HOAc -EtO)+], 294 [(M -HOAc)+], 354 (M+).…”

Section: Methodsmentioning

confidence: 99%

“…), 2.1 (s, CH3CO), 2.47 (s, CH3 of toluyl), 2.0-2.8 (m, 2 H2., H6. ), 4.0 (m, H4,), 5.15 (m, Hy), 6.18 (t, Jv,2-= 7 Hz, Hr), l,2,5,6-Tetradeoxy-l-(thymin-l-yl)-/3-D-erythro-heptofuranuronic acid (15). A solution of ethyl 3-O-acetyl-l,2,5,6tetradeoxy-l-(thymin-l-yl)-/3-D-eryihro-hept-5-enofuranuronate (3; 2.4 g, 6.7 mmol) in 1 N NaOH (52 mL) was heated at 80 °C for 20 h, deionized with Amberlite IR-120 (H), evaporated to about 6 mL, and purified by preparative thin-layer chromatography on Analtech Avicel cellulose plates (1-mm thickness) developed in BuOH-HOAc-H20 (5:2:3).…”

Section: Methodsmentioning

confidence: 99%

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Diazomethyl ketone derivatives of pyrimidine nucleosides

Thomas¹

1981

J. Org. Chem.

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l,5,6,8-Tetradeoxy-8-diazo-/3-D-eryfhro-7-octulofuranosylthymine (20) and 5,6,8-trideoxy-8-diazo-d-D-nbo-7octulofuranosyluracil (31), pyrimidine nucleosides containing the reactive diazomethyl ketone function, were prepared from thymidine and uridine via their 5'-aldehydes 2 and 22 by the Wittig reaction with (carbalkoxymethylene)triphenylphosphoranes followed by modification of the side chains of 3, 4, and 23 and blocking of the acidic NH of the pyrimidine rings.

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“…(s, 5-CH3), 2.07 (s, CHgCO), 2.S-2.7 (m, 2 *), 4.15 (m, CH3CH2), 4.58 (m, H4. ), 5.2 (m, Ha,), 6.07 (d, H6. ), 6.25 (t, Hr), 7.05 (dd, H5•), 7.6 (H6).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Diazomethyl ketone derivatives of pyrimidine nucleosides

Thomas¹

1981

J. Org. Chem.

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“…Wittig-type reactions of nucleoside 5'-aldehydes with electronegatively substituted ylides have provided several 6'-substituted-5',6'-unsaturated hexofuranosyl nucleosides (7)(8)(9)(10)(11).…”

Section: Introductionmentioning

confidence: 99%

Nucleic acid related compounds. 63. Synthesis of 5′-deoxy-5′-methyleneadenosine and related Wittig-extended nucleosides

Wnuk¹,

Robins²

1991

Can. J. Chem.

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STANISLAW F. WNUK and MORRIS J. ROBINS. Can. J. Chem. 69, 334 (1991). Treatment of the purified 5'-aldehyde (2a) (derived from 6-N-benzoyl-2',3'-0-isopropylideneadenosine ( l a ) ) with methylenetriphenylphosphorane and successive deprotection with ammonia and acid gave 9-(5,6-dideoxy-@-D-ribo-hex-5-enofuranosy1)adenine (5'-deoxy-5'-methyleneadenosine) (4). Oxidation of l a or 2',3'-0-isopropylideneadenosine (16) and treatment of the crude 5'-aldehydes (2a or 26) with (p-toluenesulfonylmethylene)triphenylphosphorane gave high yields of the 5'-deoxy-5'-tosylmethylene derivatives (5a or 56). Removal of the tosyl group from 56 to give 3 6 was effected with tributylstannyllithium, but sulfone cleavage by the usual reductive methods failed. Reduction and deprotection of 5 a or 56 gave 9-[5,6-dideoxy-6-(p-toluenesulfonyl)-~-~-ribo-hexofuranosyl]adenine (6b). Isomerization of the vinyl tosyl (56) to a 4',5'-unsaturated allylic tosyl derivative (7) occurred under cleavage conditions and in solutions of aqueous or organic bases.

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Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: TheMoffatt,Swern, and Related Oxidations

Tidwell

1990

Organic Reactions

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The use of dimethyl sulfoxide as an oxidizing agent began with the discoveries by Kornblum and co‐workers that certain α‐bromo ketones were converted into glyoxals under mild conditions by treatment with dimethyl sulfoxide, and that primary tosylates such as n ‐octyl tosylate were converted into the corresponding aldehydes using dimethyl sulfoxide and sodium bicarbonate at 150° for 3 minutes. The initial step of the reactions involves a displacement by dimethyl sulfoxide giving an alkoxysulfonium ion and this species undergoes a 1,2 elimination assisted by base to give the carbonyl product A few years later it was discovered that alcohols were oxidized at room temperature to carbonyl compounds by dimethyl sulfoxide, dicyclohexylcarbodiimide (DCC), and phosphoric acid. This reaction was immediately recognized as an effective and mild procedure for sensitive substrates, and the extensive studies by this group and the development of alternative variations elsewhere have been the subject of several earlier reviews. The course of the Moffatt procedure is summarized. The key intermediate in this process is the oxysulfonium ylide, which appears to be common to all of the variations of dimethyl sulfoxide oxidations, and which reacts intramolecularly to give the products. Other related procedures that were soon developed utilize dimethyl sulfoxide activated by acetic anhydride, phosphorus pentoxide, sulfur trioxide/pyridine complex, and chlorine. Reaction of alcohols with phosgene to give chloroformates which react with dimethyl sulfoxide to give alkoxysulfonium ions, followed by reaction with triethylamine, also effects oxidation. The reaction of the complexes of dimethyl sulfide and chlorine or N ‐chlorosuccinimide (NCS) with alcohols is proposed to give the same alkoxysulfonium complexes, which are efficiently converted into carbonyl products upon addition of triethylamine. Electrochemical activation of sulfides has also been successfully utilized. The activation of dimethyl sulfoxide is effected by many reagents, and these reactions as well as those involving activated sulfides evidently involve the alkoxysulfonium ion and the decisive oxidation step which occurs via the alkoxysulfonium ylide in all the reactions. Activation of dimethyl sulfoxide by oxalyl chloride, has become the most used of these oxidation procedures, but several of the other methods are also convenient and efficient.

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Recherche d'analogues de nucléosides à activité antivirale

Cited by 14 publications

References 16 publications

Diazomethyl ketone derivatives of pyrimidine nucleosides

Diazomethyl ketone derivatives of pyrimidine nucleosides

Nucleic acid related compounds. 63. Synthesis of 5′-deoxy-5′-methyleneadenosine and related Wittig-extended nucleosides

Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: TheMoffatt,Swern, and Related Oxidations

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