Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions.
Science
; 355(6321): 162-166, 2017 01 13.
Article
em En
| MEDLINE
| ID: mdl-28082586
ABSTRACT
Carbohydrates are involved in nearly all aspects of biochemistry, but their complex chemical structures present long-standing practical challenges to their synthesis. In particular, stereochemical outcomes in glycosylation reactions are highly dependent on the steric and electronic properties of coupling partners; thus, carbohydrate synthesis is not easily predictable. Here we report the discovery of a macrocyclic bis-thiourea derivative that catalyzes stereospecific invertive substitution pathways of glycosyl chlorides. The utility of the catalyst is demonstrated in the synthesis of trans-1,2-, cis-1,2-, and 2-deoxy-ß-glycosides. Mechanistic studies are consistent with a cooperative mechanism in which an electrophile and a nucleophile are simultaneously activated to effect a stereospecific substitution reaction.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Tioureia
/
Glicosídeos
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article