Chemische Reaktionen und Derivatisierungen ungesättigter Zucker

Heyns, Kurt; Feldmann, J.

doi:10.1002/star.19800320203

Cited by 2 publications

(1 citation statement)

References 102 publications

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“…[28] After peracetylation and bromination at the anomeric center, reduction with zinc and N-methylimidazole led to glucal 7 in a yield of 67 % and to galactal 8 in a yield of 34 %. The fluorine atoms were introduced by the addition of 2 equiv.…”

Section: Synthesis Of Fluorinated Ndp Sugars 24-26mentioning

confidence: 99%

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Wolf¹,

Berrio²,

Meier³

2011

Eur J Org Chem

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Recently, we reported an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose‐, glucose‐6‐sulfate‐, L‐galactose‐, and 2‐fluoroglycopyranoside‐containing NDP sugars are presented, as well as the synthesis of NDP sugars with non‐natural nucleosides. The reactions described gavestereoisomerically defined NDP sugars in high yields and short reaction times.

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Section: Synthesis Of Fluorinated Ndp Sugars 24-26mentioning

confidence: 99%

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Wolf¹,

Berrio²,

Meier³

2011

Eur J Org Chem

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Olefin Synthesis by Deoxygenation of Vicinal Diols

Block

1984

Organic Reactions

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Since the discovery in 1963 that 1,3‐dioxolane‐2‐thiones (cyclic thionocarbonates) undergo stereospecific fragmentation to olefins on heating with trivalent phosphorus compounds (the Corey–Winter reaction), a variety of approaches have been developed for the regio‐ and stereospecific (or stereo‐selective) deoxygenation of vicinal diols based on syn elimination from cyclic derivatives. These methods have been particularly useful in synthesizing substrates with delicate structural features such as strained and twisted olefins, unsaturated carbohydrates, macrocyclic lactones, lipids, and polyenes, as well as in establishing the stereochemistry of diol functions in natural products. This chapter deals primarily with deoxygenation of vicinal diols via cyclic species with X = C, P, Ti, W, or S (suitably functionalized). Brief coverage is given to deoxygenation processes that do not involve cyclic intermediates, whereas routes proceeding via oxiranes or vic ‐dihalides as separately isolated intermediates are excluded from consideration. The stereochemical equilibration of vicinal diols and the conversion of vicinal hydroxy thiols and dithiols to olefins are also covered in this chapter. Brief reviews have appeared in the literature of the Corey–Winter reaction and of the general topic of deoxygenation of vicinal diols.

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Chemische Reaktionen und Derivatisierungen ungesättigter Zucker

Abstract: Es wird eine zusammenfassende Übersicht über die vielfältigen chemischen Reaktionen dargestellt, die sich bei den Umsetzungen ungesättigter Zucker mit verschiedenartigen Reaktionspartnern ergeben und die zahlreiche interessante Synthesewege für Derivatisierungen ermöglichen.

Cited by 2 publications

References 102 publications

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Olefin Synthesis by Deoxygenation of Vicinal Diols

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