Stereospecific Vorbrueggen-like reactions of 1,2-anhydro sugars. An alternative route to the synthesis of nucleosides

Chow, Ken; Danishefsky, Samuel J.

doi:10.1021/jo00300a049

Cited by 84 publications

(24 citation statements)

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“…However, only limited success has been reported for nucleoside synthesis with privileged O-glycosylation donors, including glycosyl chlorides/bromides, [5,9] trichloroacetimidates, [10] phosphites, [11] sulfoxides, [12] thioglycosides, [13] n-pentenyl glycosides, [14] and sugar 1,2-anhydrides. [15] One rationale is that nucleobases are poorly nucleophilic (and often poorly soluble) and thus compete unfavorably for glycosidation with other nucleo-philic species that occur in a glycosylation system, such as those derived from the leaving groups and promoters.…”

mentioning

confidence: 99%

An Efficient Approach to the Synthesis of Nucleosides: Gold(I)‐Catalyzed N‐Glycosylation of Pyrimidines and Purines with Glycosyl ortho‐Alkynyl Benzoates

et al. 2011

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confidence: 99%

An Efficient Approach to the Synthesis of Nucleosides: Gold(I)‐Catalyzed N‐Glycosylation of Pyrimidines and Purines with Glycosyl ortho‐Alkynyl Benzoates

et al. 2011

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“…In 1990 Danishefsky and Chow proposed the epoxidation of furanoid glycals and showed their application towards the synthesis of nucleosides. 8 The epoxidation of furanoid glycal 65b with DMDO (dimethyldioxirane) was highly face selective to give 568. The treatment of the epoxide 568 with (TMS) 2 thymine provided a mixture of 569 (52% yield) and 570 (30% yield).…”

Section: Synthesis Of N-nucleosidesmentioning

confidence: 99%

The evolution of comprehensive strategies for furanoid glycal synthesis and their applications

Pal

Shaw

2017

RSC Adv.

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including natural products with various biological activities since their discovery in 1963 by Ness and Fletcher. In this review on furanoid glycals, efforts are made to exhaustively compile the work centered on synthesis and utility of furanoid glycals since the inception to date. This review aims to highlight the importance of furanoid glycals and the strategies developed over the years for their synthesis. Attention has also been focused on the use of these furanoid glycals toward the synthesis of natural and unnatural products including C-and N-nucleosides of biological importance. Apart from that, efforts are also devoted to cover the significant applications of these furanoid glycals for stereoselective synthesis of various cyclic and acyclic key intermediates of significant interest.

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“…The halogen (chloride or bromide) of acarefully prepared fully protected a-halogenose can be displaced in an S N 2f ashionb yt he metals alto fanucleobase to yield the desired b-2'-deoxynucleoside ( Figure 1b). [8] One commonly known method to access ah ost of pyranosyl glycosides, studied extensively by Danishefsky and co-workers, [9] employst he use of af ully protected intermediate 1,2-anhydrosugar that can be isolated carefully after treatment of the parentg lycal with dimethyl dioxorane (DMDO). Protected dis- accharides can then be generated through epoxide ring opening in the presence of many LAs, or other pyranosides can be synthesized by nucleophilic ring openingt oa fford (for example) fluoro, thiol, and cyano pyranosides( Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5‐O‐Monoprotected or 5‐Modified Ribose: Improved Protocol, Scope, and Mechanism

Downey

Pohl

Roithová

et al. 2017

Chemistry A European J

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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed "anhydrose") under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.

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Stereospecific Vorbrueggen-like reactions of 1,2-anhydro sugars. An alternative route to the synthesis of nucleosides

Cited by 84 publications

References 0 publications

An Efficient Approach to the Synthesis of Nucleosides: Gold(I)‐Catalyzed N‐Glycosylation of Pyrimidines and Purines with Glycosyl ortho‐Alkynyl Benzoates

An Efficient Approach to the Synthesis of Nucleosides: Gold(I)‐Catalyzed N‐Glycosylation of Pyrimidines and Purines with Glycosyl ortho‐Alkynyl Benzoates

The evolution of comprehensive strategies for furanoid glycal synthesis and their applications

Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5‐O‐Monoprotected or 5‐Modified Ribose: Improved Protocol, Scope, and Mechanism

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