Branched-chain sugar nucleosides. III. 3'-C-methyladenosine

Nutt, Ruth F.; Dickinson, Mary; Holly, Frederick W.; Walton, Edward

doi:10.1021/jo01269a019

Cited by 91 publications

(24 citation statements)

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“…RuO 4 /CCl 4 of five xylofuranosides gave the corresponding 2-and 3-uloses (Table 2.3) [315], and that of 5-O-benzoyl-1,2-O-isopropylidene-a-D-xylofuranose by the reagent to the -a-D-erythro-pentafuranos-3-ulose formed part of a synthesis of branched-chain 3¢-C-methyladenosine [316,322]. Likewise the cyclopropyl-substituted 4-C-cyclo-propyl-1,2-O-isopropyl-idene-D-xylotetrafuranose was converted to the 3-ulose [314].…”

Section: Secondary Alcohol Groups In Furanosesmentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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This is one of the most important classes of oxidation effected by Ru complexes, particularly by RuO 4 , [RuO 4 ] − , [RuO 4 ] 2− and RuCl 2 (PPh 3 ) 3 , though in fact most Ru oxidants effect these transformations. The chapter covers oxidation of primary alcohols to aldehydes (section 2.1), and to carboxylic acids (2.2), and of secondary alcohols to ketones (2.3). Oxidation of primary and secondary alcohol functionalities in carbohydrates (sugars) is dealt with in section 2.4, then oxidation of diols and polyols to lactones and acids (2.5). Finally there is a short section on miscellaneous alcohol oxidations in section 2.6.In this chapter the first of the two most important categories of oxidations catalysed by Ru complexes (the other being alkene and alkyne oxidations in Chapter 3) are considered. The approach in this and subsequent chapters differs from that of Chapter 1, concentrating here on the substrate rather than on the oxidant. The text is divided into the categories of alcohols and their oxidations. There are summaries in section 2.3.6 of systems of limited applicability which are mentioned only in Chapter 1, and in section 2.3.7 of large-scale (>1 g) oxidations.The first oxidations of alcohols by stoicheiometric RuO 4 /H 2 O were reported in 1958, of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones [1]. The first Ru-catalysed oxidation of an alcohol was reported in 1965 when Parikh and Jones used RuO 2 /aq. Na(IO 4 )/CCl 4 1 ( Table 2.3) [2] to oxidise secondary alcohol groups in carbohydrates.Oxidation of alcohols is the most frequently reviewed topic for Ru-catalysed oxidations [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Mechanisms of alcohol oxidation by Ru complexes have been reviewed [21].

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Section: Secondary Alcohol Groups In Furanosesmentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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“…However, some examples of the low reactivity of the corresponding tertiary 3'-hydroxyl have been reported in the 3'-C-β-methylribofuranosyl series. [12][13][14] In conclusion, compound 6 does not seem to be a promising substrate for 2'-modification. To solve the problem of regioselective modification of the 2',3'-diol system in 2'-C-β-methyl-D-ribonucleosides, we decided to take advantage of this low reactivity of 2'-hydroxyl group, assuming that this position could remain unprotected during 3'-modification.…”

Section: Scheme 1 Reagents and Conditions: (A) (Chmentioning

confidence: 99%

Partial acylation of cytidine and its 2'-C-methyl analogue as a tool to functionalize the ribonucleosidic 2’,3’-cis-diol system

Fogt¹,

Januszczyk²,

Onishi³

et al. 2008

Arkivoc

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Dedicated to Professor Harri Lönnberg on the occasion of his 60 th anniversary AbstractPrecisely controlled conditions of acylation and 2',3'-O-isomerization allowed to synthesize tripivaloyl derivatives of cytidine with free 2'-or 3'-hydroxyl group in a simple manner. Acylation of 2'-C-β-methylcytidine proceeded in a different way and resulted in the formation of tripivaloyl 2'-hydroxy nucleoside, or dipivaloyl 2',3'-dihydroxy compound. All these products may be applied as key intermediates in the regioselective modification of 2',3'-cis-diol system.

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“…Among them, 3Ј-b-branched chain sugar nucleoside 1-(3-C-ethynyl-b-D-ribo-pentofuranosyl)-uracil (ECyd, 3) has a remarkable antitumor activity both in vitro and in vivo and is under phase I clinical trial. [28][29][30][31][32] Although there have also been several studies on 3Ј-b-branched chain sugar nucleosides, [33][34][35][36][37][38][39][40][41][42][43] only a few 3Ј-b-branched ribonucleoside analogs, with both a hydroxyl group at the 3Ј-a-position and a carbon-substituent at the 3Ј-b-position, have been reported, and their biological activities have not been investigated in detail. This may be because efficient synthetic methods for preparing these 3Ј-b-branched ribonucleoside analogs have not been developed.…”

Section: Introductionmentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Synthetic nucleoside chemistry based on nucleoside natural products synthesis were described. First, a samarium diiodide (SmI 2 )-promoted aldol reaction with the use of a a-phenylthioketone as an enolate was developed. The characteristics of this reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside natural products, and herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside natural products, were synthesized. Next, the synthetic methodology of the caprazamycins, which are promising antibacterial nucleoside natural products, was also developed by the strategy including b bselective ribosylation without using a neighboring group participation. Our synthetic route provided a range of key analogues with partial structures to define the pharmacophore. Simplification of the caprazamycins was further pursued to develop diketopiperazine analogs.

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Branched-chain sugar nucleosides. III. 3'-C-methyladenosine

Cited by 91 publications

References 0 publications

Oxidation of Alcohols, Carbohydrates and Diols

Oxidation of Alcohols, Carbohydrates and Diols

Partial acylation of cytidine and its 2'-C-methyl analogue as a tool to functionalize the ribonucleosidic 2’,3’-cis-diol system

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

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