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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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First stereoselective synthesis of 2-deoxy-alpha-D-ribosyl-1-phosphate: novel application of crystallization-induced

Hironori Komatsu1, Hirokazu Awano

  • 1Catalysis Science Laboratory, Mitsui Chemicals, Inc., 1144 Togo, Mobara-shi, Chiba 297-0017, Japan. hironori.komatsu@mitsui-chem.co.jp

The Journal of Organic Chemistry
|July 20, 2002
PubMed

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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.