Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides

Shankar D. Markad, Shawn M. Miller, Martha Morton, Mark W. Peczuh

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Hydrolysis rates for three related methyl α-septanosides were obtained. The septanosides were synthesized via mCPBA epoxidation and methanolysis of d-mannose, d-galactose, and d-glucose-based oxepines. The rate of hydrolysis correlates with the orientation of hydroxyl groups on the septanose ring in a manner analogous to pyranosides.

Original languageEnglish (US)
Pages (from-to)1209-1212
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number8
DOIs
StatePublished - Feb 24 2010

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Hydroxyl Radical
Hydrolysis
Oxepins
Epoxidation
Mannose
Galactose
Glucose

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides. / Markad, Shankar D.; Miller, Shawn M.; Morton, Martha; Peczuh, Mark W.

In: Tetrahedron Letters, Vol. 51, No. 8, 24.02.2010, p. 1209-1212.

Research output: Contribution to journalArticle

Markad, Shankar D. ; Miller, Shawn M. ; Morton, Martha ; Peczuh, Mark W. / Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 8. pp. 1209-1212.
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