A stereoselective synthesis of methyl β-C-lactoside through the tether approach
✍ Scribed by Gilles Rubinstenn; Jean-Maurice Mallet; Pierre Sinaÿ
- Book ID
- 104259252
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 252 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Methyl ~-C-lactoside ([3-D-Galp-C-(l-->4)-~-Glcp-OMe) is stereoselectively synthesized by radical coupling of phenyl Se-[~ -D-galactopyranoside 5 onto exo-methylene-sugar 4, which are temporarily connected through a silaketal tether.
📜 SIMILAR VOLUMES
A non-covalent version of the intramolecular aglycon delivery methodology has been demonstrated for the stereoselective formation of b-D-mannopyranoside in the presence of lanthanide(III) triflate.
An efficient method for preparing both 1α-and 1β-C-glucosides having a 3-hydroxypropyl group at the anomeric position via a radical cyclization reaction with an allylsilyl tether was developed. The stereoselectivity of the radical cyclization can be controlled by the conformation of the pyranose rin