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A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives
- Source :
- Tetrahedron Letters. 47:3081-3084
- Publication Year :
- 2006
- Publisher :
- Elsevier BV, 2006.
-
Abstract
- A stereodivergent synthesis of N-alkylated 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives has been achieved from a protected 1-deoxynojirimycin intermediate having two free OH groups tactically positioned at C-2 and C-4. The inversion of configuration of the secondary alcohols was performed by way of a Swern oxidation followed by a highly diastereoselective reduction using NaBH 4 or L-Selectride.
Details
- ISSN :
- 00404039
- Volume :
- 47
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........5459f9ab5d56ead7df91d450d0407cb8