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Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.
Yalamanchili, Subbarao; Nguyen, Tu-Anh V; Pohl, Nicola L B; Bennett, Clay S.
Afiliação
  • Yalamanchili S; Department of Chemistry, Tufts University, 62 Talbot Ave, Medford, MA 02145, USA. Clay.Bennett@tufts.edu.
  • Nguyen TV; Department of Chemistry, Tufts University, 62 Talbot Ave, Medford, MA 02145, USA. Clay.Bennett@tufts.edu.
  • Pohl NLB; Department of Chemistry, Indiana University, 212 S. Hawthorne Dr, Bloomington, IN, 47405, USA. npohl@indiana.edu.
  • Bennett CS; Department of Chemistry, Tufts University, 62 Talbot Ave, Medford, MA 02145, USA. Clay.Bennett@tufts.edu.
Org Biomol Chem ; 18(17): 3254-3257, 2020 05 06.
Article em En | MEDLINE | ID: mdl-32293636
An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to prevent unwanted exotherms and required shorter reaction times.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligossacarídeos / Desoxiglucose / Técnicas de Química Sintética Idioma: En Ano de publicação: 2020 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligossacarídeos / Desoxiglucose / Técnicas de Química Sintética Idioma: En Ano de publicação: 2020 Tipo de documento: Article