Efficient palladium(0)-catalyzed synthesis of alkenyl 1-thioglycosides and thiodisaccharides

Article abstract of DOI:10.1080/07328300008544118

Unsaturated thiodisaccharides are obtained in good yields by alkylation of ethyl α-O-Δ2-glycosides, having a leaving group at C-4, with various thiocarbohydrates in the presence of a catalytic amount of palladium(O). The reaction is regio- and stereospecific for the α-erythro enoside, and only stereospecific in the case of the α-threo enoside, alkylation occurring at C-4 and C-2. In all cases, only the β-anomer is formed.

Full text of DOI:10.1080/07328300008544118

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Journal of Carbohydrate Chemistry
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Efficient Palladium(0)-
Catalyzed Synthesis of
Alkenyl 1-Thioglycosides and
Thiodisaccharides
Anna Zawisza , Boguslaw Kryczka , Paul Lhoste , Stanislaw
Porwanski & Denis Sinou
a Department of Organic and Applied Chemistry , University
of Lodz , ul. Narutowicza 68, 90-136 Lodz, Poland
b Department of Organic and Applied Chemistry , University
of Lodz , ul. Narutowicza 68, 90-136 Lodz, Poland
c Laboratoire de Synthèse Asymétrique, associé au CNRS ,
CPE Lyon, Université , Claude Bernard Lyon 1, 43, boulevard
du 11 novembre 1918, 69622 Villeurbanne, Cédex, France E-
mail:
d Department of Organic and Applied Chemistry , University
of Lodz , ul. Narutowicza 68, 90-136 Lodz, Poland
e Laboratoire de Synthèse Asymétrique, associé au CNRS ,
CPE Lyon, Université , Claude Bernard Lyon 1, 43, boulevard
du 11 novembre 1918, 69622 Villeurbanne, Cédex, France E-
mail:
Published online: 27 Feb 2008.
To cite this article: Anna Zawisza , Boguslaw Kryczka , Paul Lhoste , Stanislaw Porwanski
& Denis Sinou (2000) Efficient Palladium(0)-Catalyzed Synthesis of Alkenyl 1-Thioglycosides
and Thiodisaccharides, Journal of Carbohydrate Chemistry, 19:7, 795-804, DOI:
10.1080/07328300008544118
To link to this article: http://dx.doi.org/10.1080/07328300008544118
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