Synthesis of β-C-galactosyl d- and l-alanines

V. Narasimharao Thota, Jacquelyn Gervay-Hague, Suvarn S. Kulkarni

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Synthesis of β-C-d-galactosyl d- and l-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and SN2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

Original languageEnglish (US)
Pages (from-to)8132-8139
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number40
DOIs
StatePublished - Oct 28 2012

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Grignard reactions
Mesylates
Cyclization
Iodides
alanine
Alanine
iodides
alcohols
actuators
Alcohols
synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Synthesis of β-C-galactosyl d- and l-alanines. / Thota, V. Narasimharao; Gervay-Hague, Jacquelyn; Kulkarni, Suvarn S.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 40, 28.10.2012, p. 8132-8139.

Research output: Contribution to journalArticle

Thota, V. Narasimharao ; Gervay-Hague, Jacquelyn ; Kulkarni, Suvarn S. / Synthesis of β-C-galactosyl d- and l-alanines. In: Organic and Biomolecular Chemistry. 2012 ; Vol. 10, No. 40. pp. 8132-8139.
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