Sugar lactams and lactim ethers, useful precursors of cyclic amidines, from intramolecular nucleophilic displacements
✍ Scribed by Veronique Moreaux; Heidi Warren; J Michael Williams
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 215 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The cyclisation of the conjugate base of N-aryl-2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-Dgulonamides gave the D-allonolactam acetals. Sodium methoxide-promoted cyclisation of 2,3:5,6-di-Oisopropylidene-4-O-methanesulfonyl-D-mannononitrile gave the D-talonolactim ether. Tetrazole formation without isolation of the intermediate azide was illustrated by the conversion of the aforementioned nitrile sulfonate into the D-talonotetrazole. Cyclic amidines were prepared from the lactam and lactim ether derivatives. The Dallono derivatives were also converted into D-ribono-1,4 lactam and amidine derivatives.