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 journalArticlepeer-review

10 Scopus citations


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
Issue number8
StatePublished - Feb 24 2010
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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