2'3'-Carbonates in the synthesis of uridine 5'-deoxy and 2',5'-dideoxy derivatives

Hein, L.; Draser, P; Beránek, Jaroslav

doi:10.1093/nar/3.4.1125

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…[19] 2Ј,3Ј-Di-O-acetyl-5Ј-bromouridine (11) was prepared in 60 % yield from 10 by replacement of the mesyloxy group by bromine, accomplished by treatment with tetrabutylammonium bromide in DMF at 130°C. [19] Subsequent tributyltin hydride reduction of 11 in a mixture of toluene and ethanol at reflux with initiation with AIBN afforded 2Ј,3Ј-di-O-acetyl-5Ј-deoxyuridine (12) in 65 % yield. [19] Compound 12 was deprotected with sodium methoxide in anhydrous MeOH to afford 5Ј-deoxyuridine (13) in 92% yield.…”

Section: Chemo-enzymatic Synthesis Of 5ј-deoxy-5-fluorouridine (Doxifmentioning

confidence: 99%

“…[19] Subsequent tributyltin hydride reduction of 11 in a mixture of toluene and ethanol at reflux with initiation with AIBN afforded 2Ј,3Ј-di-O-acetyl-5Ј-deoxyuridine (12) in 65 % yield. [19] Compound 12 was deprotected with sodium methoxide in anhydrous MeOH to afford 5Ј-deoxyuridine (13) in 92% yield. [20] This compound was used, after purification, for enzymatic (pyrimidine/pyrimidine) transglycosylation with 5-fluorouracil.…”

Section: Chemo-enzymatic Synthesis Of 5ј-deoxy-5-fluorouridine (Doxifmentioning

confidence: 99%

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A Versatile Synthesis of 5′‐Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors

et al. 2009

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We describe a chemo-enzymatic synthesis of modified nucleosides through lipase-catalyzed hydrolysis of their peracetylated precursors. It was found from screening of a large number of substrates that these enzymes' regioselectivities were affected by the sugar and the nucleobase structures. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monodeprotected purine and pyrimidine nucleosides useful as intermediates for the synthesis of high-value nu-

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Section: Chemo-enzymatic Synthesis Of 5ј-deoxy-5-fluorouridine (Doxifmentioning

confidence: 99%

Section: Chemo-enzymatic Synthesis Of 5ј-deoxy-5-fluorouridine (Doxifmentioning

confidence: 99%

A Versatile Synthesis of 5′‐Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors

et al. 2009

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“…(444,445) I, 1'-Carbonyldi(2-methylimidazole) was also used to afford (187). (446) Uridine 2',3'-thionocarbonate was converted to the 2',3'-dimethylorthocarbonate by treatment with silver oxide in methanol, which was further converted to the cyclic carbonate by mild acid treatment.…”

Section: /mentioning

confidence: 99%

Synthesis and Reaction of Pyrimidine Nucleosides

Ueda

1988

Chemistry of Nucleosides and Nucleotides

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Chemical Transformations of the Sugar Moiety of Nucleosides

Moffatt¹

1979

Nucleoside Analogues

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The last two decades have witnessed the proliferation of a rather vast literature concerning the synthesis and biological properties of nucleoside analogues. These interesting compounds can be roughly subdivided into two major groups--those containing modified heterocyclic bases, and those in which the sugar moiety has been altered and is no longer ribose or 2-deoxyribose as found in nucleic acids. Base analogues have in general been prepared either via N-glycosidation of suitably modified heterocycles or by structural transformations of the base moiety in existing nucleosides. Both of these approaches will be considered in detail during this meeting by my colleagues Drs. VorbrUggen, Robins and Townsend. In a related way, nucleosides containing modified carbohydrate moieties have frequently been prepared via glycosidation of an appropriate purine or pyrimidine base with a suitable derivative of the desired sugar. Alternatively, a great deal of effort has been devoted to the development of specific chemical transformations suitable for introducing the desired modifications into the sugar moiety of intact nucleosides. It is this latter approach that has particularly fascinated the group in our laboratory and that I wish to review for you today. The subject is, however, a rather vast one, encompassing an enormous number of references, and accordingly I must, of necessity, be somewhat selective in what I specifically mention. Accordingly, I have decided to restrict my attentions to analogues of pentofuranosyl nucleosides and to make almost no mention of hexose derivatives tContribution No. 527 from the Institute

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2'3'-Carbonates in the synthesis of uridine 5'-deoxy and 2',5'-dideoxy derivatives

Cited by 7 publications

References 8 publications

A Versatile Synthesis of 5′‐Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors

A Versatile Synthesis of 5′‐Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors

Synthesis and Reaction of Pyrimidine Nucleosides

Chemical Transformations of the Sugar Moiety of Nucleosides

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