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Asymmetric Synthesis of 1,3-Dithiolane Nucleoside Analogues

✍ Scribed by Romualdo Caputo; Annalisa Guaragna; Giovanni Palumbo; Silvana Pedatella

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
98 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We report the ready asymmetric synthesis of nucleoside analogues containing a 1,3‐dithiolane ring that mimics the sugar moiety of natural nucleosides. The synthesis is accomplished in three main steps from benzoyloxyethanal 1,3‐dithiolane, the key step being its conversion into a chiral monosulfoxide by a modified Sharpless sulfo‐oxygenation reaction. The nucleoside analogues were obtained in good overall yields and with excellent enantiomeric excesses. (Β© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Asymmetric Synthesis of 1,3-Dithiolane N
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✍ Romualdo Caputo; Annalisa Guaragna; Giovanni Palumbo; Silvana Pedatella πŸ“‚ Article πŸ“… 2003 πŸ› John Wiley and Sons βš– 156 KB πŸ‘ 2 views

## Abstract For Abstract see ChemInform Abstract in Full Text.

A New Strategy for the Asymmetric Synthe
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A ready asymmetric synthesis of 3Ј-oxathionucleosides has overall yield and considerable enantiomeric excesses. It represents a general synthetic path to prepare a wide range been accomplished in three main steps from benzoyloxyethanal. The synthesis is characterized by high of heterosubstituted sul