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α-Selective Glucosylation Can Be Achieved with 6-O-para-Nitrobenzoyl Protection.
Trinderup, Helle H; Juul-Madsen, Line; Press, Laura; Madsen, Michael; Jensen, Henrik H.
Affiliation
  • Trinderup HH; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
  • Juul-Madsen L; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
  • Press L; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
  • Madsen M; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
  • Jensen HH; Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
J Org Chem ; 87(21): 13763-13789, 2022 11 04.
Article in En | MEDLINE | ID: mdl-36206491
ABSTRACT
A systematic study of the effect of various 6-O-acyl groups on anomeric selectivity in glucosylations with thioglycoside donors was conducted. All eight different esters were found to induce moderate-to-high α-selectivity in glucosylation with l-menthol with the best being 6-O-p-nitrobenzoyl. The effect appears to be general across various glucosyl acceptors, glucosyl donor types, and modes of activation. No evidence was found in favor of distal participation.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Esters Language: En Journal: J Org Chem Year: 2022 Document type: Article Affiliation country:
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Esters Language: En Journal: J Org Chem Year: 2022 Document type: Article Affiliation country: