Two synthetic routes to 2′,3′-dideoxy-3′-C-(hydroxymethyl)-4′-thionucleosides

Mann, John; Tench, Allen J.; Weymouth‐Wilson, Alexander C.; Shaw‐Ponter, S.; Young, Robert J.

doi:10.1039/p19950000677

Cited by 19 publications

(5 citation statements)

References 16 publications

(1 reference statement)

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“…The Mann et al [62] planned two alternative routes for the synthesis of 2', 3'-dideoxy-3'-C-hydroxymethyl-4'-thionucleosides. One starts with the synthesis of butyrolactone derivative 4-116, via the stereo-and regioselective photocatalyzed addition of MeOH to butenolide 4-115 (Scheme 4-10).…”

Section: ' 3'-dideoxy-4'-thionucleosidesmentioning

confidence: 99%

Recent Advances in 4-Thionucleosides as Potential Antiviral and Antitumor Agents

Gunaga¹,

Moon²,

Choi³

et al. 2004

CMC

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The classical 4'-oxonucleoside analogs exhibit interesting biological activities such as antibiotic, antiviral and antitumor, which are believed to be the result of inhibition of the viral or cellular DNA or RNA polymerase after being converted to their corresponding 5'-triphosphates. However, the activity of 4'-oxonucleosides were limited by their susceptibility to degradation by nucleoside phosphorylases or acid hydrolysis. This aspect called for the chemical modification of the carbohydrate portion. This compulsion led to two kinds of strategies; (1) replacement of the 4'-oxygen by the methylene group - carbocyclic nucleosides; (2) replacement of the 4' oxygen by sulphur-4'-thionucleosides. This group has also conferred the resistance to the nucleoside cleavage. Although, there were some pioneering work on 4'-thionucleosides in 1960s and 1970s, the interest in this group of compounds was rekindled by the antiviral activities of 2'-deoxy-4'-thionucleosides reported independently by Secrist et al. and Walker et al. Subsequent contributions by the other authors, enhanced its standing as an important class of antiviral agents. Following is a reasonably exhaustive account of this class of compounds reported after 1990.

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Section: ' 3'-dideoxy-4'-thionucleosidesmentioning

confidence: 99%

Recent Advances in 4-Thionucleosides as Potential Antiviral and Antitumor Agents

Gunaga¹,

Moon²,

Choi³

et al. 2004

CMC

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“…The same team has investigated synthetic routes to obtain 2',3'-dideoxy-3'-hydroxymethyl-4'-thionucleosides 120 (Chart 10). 64 The initially chosen pathway starting from HBO was not efficient, so a longer route has been selected starting from diethyl (S,S)tartrate. Unfortunately, the tested thionucleosides did not exhibit any activity.…”

Section: Nucleosides Derivatives Starting From Hbomentioning

confidence: 99%

“…Upon absorption of light (a photon), molecules reach specific electronically excited states corresponding to precise electron distributions, leading to original chemical properties and reactivities. As photochemical reactions generally occur without additional reagents, the byproduct formation is dramatically reduced, revealing photochemistry as a high-potential approach in green chemistry. − Photoadditions of alcohols, − acetals, ,,, or amines to HBO have been reported in the literature.…”

Section: Reactivity Studies Of Hbo and Its Derivativesmentioning

confidence: 99%

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Flourat

Haudrechy

Allais

et al. 2019

Org. Process Res. Dev.

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Chirality is greatly sought for pharmaceutical compounds or fragrance and flavors.(S)-γ-hydroxymethyl-α,β-butenolide, aka HBO, is a chiral (5H)-furanone providing a polarized double bond, a lactone ring and a primary alcohol as playground for synthetic chemists. This molecule has been used for forty years in a wide range of synthetic pathways to natural and/or bioactive molecules. Its own synthesis, always from biosourced product, has also significantly evolved and could be now achieved both at large scale and by applying Green Chemistry principles. This review will explore the syntheses, the reactivity and the uses of HBO.

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“…Samuelsson and coworkers started from the optically active compound 309 via the corresponding epithio derivative 375.89 Compound 309 was converted into the 2,3epithio derivative 375 in 67% yield by reacting with thiourea in MeOH for 5 days. The episulfide 375 was regioselectively opened by allylmagnesium bromide.Mann and coworkers started from the known epoxide 159 to produce 385 90. The chiral epoxide 159 was treated with allylmagnesium bromide at -50 °C to provide alcohol 381.…”

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confidence: 99%

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

Ichikawa¹,

Kato²

2004

Synthesis

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Since the naturally occurring unusual nucleoside oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the efforts to synthesize oxetanocin A from the first synthesis in 1987 and the related unusual nucleosides with bis(hydroxymethyl)-branched sugars, including our works in this area. 7Thietanosyl Nucleosides

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Two synthetic routes to 2′,3′-dideoxy-3′-C-(hydroxymethyl)-4′-thionucleosides

Cited by 19 publications

References 16 publications

Recent Advances in 4-Thionucleosides as Potential Antiviral and Antitumor Agents

Recent Advances in 4-Thionucleosides as Potential Antiviral and Antitumor Agents

(S)-γ-Hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity, and Applications

Syntheses of Oxetanocin A and Related Unusual Nucleosides with Bis(hydroxymethyl)-branched Sugars

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