1,2- trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis.
Org Lett
; 21(4): 1221-1225, 2019 02 15.
Article
em En
| MEDLINE
| ID: mdl-30693782
ABSTRACT
The use of 2- O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2- trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2- O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2- O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article