Synthesis of 2′,3′-dideoxy-2′,3′-α-methanocytidine

Beard, Andrew R.; Butler, P. I.; Mann, John; Partlett, N. K

doi:10.1016/0008-6215(90)80130-u

Cited by 35 publications

(10 citation statements)

References 5 publications

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“…Photocycloaddition of 2(5 H )-Furanones 1a − e to Acetylene. Compounds 1a ,5a 1c , 1d , and 1e 5b were synthesized following procedures described in the literature. The new furanone 1b was easily prepared in 93% yield by the reaction of ( S )-5-hydroxymethyl-2(5 H )-furanone with (−)-menthyl chloroformate and pyridine in CH 2 Cl 2 .…”

Section: Resultsmentioning

confidence: 99%

Photochemical [2 + 2] Cycloaddition of Acetylene to Chiral 2(5H)-Furanones

et al. 2003

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The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C(2)-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.

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Section: Resultsmentioning

confidence: 99%

Photochemical [2 + 2] Cycloaddition of Acetylene to Chiral 2(5H)-Furanones

et al. 2003

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“…Finally, a plethora of conformationally restricted nucleosides has been synthesized for potential antiviral activity. ,, Among them, nucleoside analogues incorporating a fused methylene group, oxirane, oxetane, or perhydro-1,3-oxazine inhibit HIV replication.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Characterization of Pyrimidine Bi- and Tricyclic Nucleosides with Sugar Puckers Conformationally Locked into the Eastern Region of the Pseudorotational Cycle

et al. 2003

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Reaction of 5'-O-tosyl TSAO-m(3)T (1) with amines has led to the synthesis of new classes of bi- and tricyclic nucleosides. Full details about the synthesis of these compounds and a plausible mechanism to explain their obtention are reported. In addition, we describe the development of a second, more efficient, and higher yielding synthetic route as a general approach for the synthesis of some of these bicyclic nucleosides. To study the conformational behavior of the bi- and tricyclic nucleosides described in this paper, intensive NMR investigations and molecular modeling studies were performed. Conformational analysis indicates that the furanose ring of the compounds described here prefers the eastern side of the pseudorotation cycle with the base substituents preferentially in the anti range. The torsion angle gamma describing the C-4'[bond]C-5' is found to prefer the +sc range. These compounds represent a novel class of E-type conformationally restricted bicyclic ribo-nucleosides containing a [3.3.0]-fused carbohydrate moiety. The bicyclic nucleosides described herein present an interesting potential for diverse and selective chemical treatments on the 2'-hydroxyl and/or the functionalities incorporated at the bridge between C-3' and C-5'.

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“…Thus, an iterative computation confirmed the trans relationship between H2 and H3 in (10) and gave the parameters described in Table. The first hypothesis we considered for the stereochemistry of compound (9) was a cis relationship for the two cyclopropyl substituents, but no convergence was reached which involved parameters according to this hypothesis. In fact a 500 MHz spectrum from which parameters have been extracted by first-order analysis, showed that in this compound too, H2 and H3 are in a trans relationship as for compound (10).…”

Section: Resultsmentioning

confidence: 52%

1′, 2′-Seco-2′,3′-Dideoxynucleoside Analogues: Synthesis and Antiviral Evaluation of Racemic Trans-[1′, 5′-Dihydroxy 3′, 4′-methylenylpent-2′-oxy)methyl] Nucleosides

Azymah

Chavis

Fruchier

et al. 1992

Nucleosides and Nucleotides

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CNRS n'458, 8 rue de 1'Ecole Normale, 34053 Montpellier Cedex 1 (France).Abstract: Reaction of (f)but-3-en-l,2-diol (3) with ethyl diazoacetate afforded two cyclopropyl compounds ( 5 ) and (6). Their relative rruns stereochemistry at C-2 and C-3 has been determined by high-field and computational NMR spectroscopy. (+)Trans-1-( 1',5'-dihydroxy-3',4'-methylenyl-pent-2'-oxy)methyl]thymine (Id) or -cytosine (lb) and(+)rrcms-9-(1',5'-dihydroxy-3',4'-methylenylpent-2'-oxy)-methylladenine (la) or -guanine (lc) have been obtained through a regiospecific alkylation procedure and their antiviral evaluation is reported.

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Synthesis of 2′,3′-dideoxy-2′,3′-α-methanocytidine

Cited by 35 publications

References 5 publications

Photochemical [2 + 2] Cycloaddition of Acetylene to Chiral 2(5H)-Furanones

Photochemical [2 + 2] Cycloaddition of Acetylene to Chiral 2(5H)-Furanones

Synthesis and Structural Characterization of Pyrimidine Bi- and Tricyclic Nucleosides with Sugar Puckers Conformationally Locked into the Eastern Region of the Pseudorotational Cycle

1′, 2′-Seco-2′,3′-Dideoxynucleoside Analogues: Synthesis and Antiviral Evaluation of Racemic Trans-[1′, 5′-Dihydroxy 3′, 4′-methylenylpent-2′-oxy)methyl] Nucleosides

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