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Stereoselective Access to Iminosugar C , C -Glycosides from 6-Azidoketopyranoses.
- Source :
-
Organic letters [Org Lett] 2022 Jul 01; Vol. 24 (25), pp. 4542-4546. Date of Electronic Publication: 2022 Jun 22. - Publication Year :
- 2022
-
Abstract
- We report the synthesis of iminosugar C , C -glycosides starting from 6-azidoketopyranoses. Their Staudinger-azaWittig-mediated cyclization provided bicyclic N , O -acetals, which were stereoselectively opened with AllMgBr to afford β-hydroxyazepanes with a quaternary carbon α to the nitrogen. Their ring contraction via a β-aminoalcohol rearrangement produced the six-membered l-iminosugars with two functional handles at the pseudoanomeric position. Inversion of the free OH at the azepane level furnished the d-iminosugars.
- Subjects :
- Cyclization
Glycosides
Imino Sugars
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 24
- Issue :
- 25
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 35731688
- Full Text :
- https://doi.org/10.1021/acs.orglett.2c01560