Total synthesis of everninomicin 13,384-1--Part 4: explorations of methodology; stereocontrolled synthesis of 1,1'-disaccharides, 1,2-seleno migrations in carbohydrates, and solution- and solid-phase synthesis of 2-deoxy glycosides and orthoesters.
Chemistry
; 6(17): 3166-85, 2000 Sep 01.
Article
de En
| MEDLINE
| ID: mdl-11002995
Methods for the stereocontrolled construction of 1,1'-disaccharides, 2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1'-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides with DAST led to 2-phenylselenoglycosyl fluorides which reacted with carbohydrate acceptors to afford, stereoselectively, 2-phenylselenoglycosides. The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals.
Recherche sur Google
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Glucides
/
Diholoside
/
Hétérosides
/
Aminosides
/
Antibactériens
Langue:
En
Journal:
Chemistry
Sujet du journal:
QUIMICA
Année:
2000
Type de document:
Article
Pays d'affiliation:
États-Unis d'Amérique
Pays de publication:
Allemagne