Preparation of acylated pyranoid glycals in neutral aqueous medium by using chromium(II) complexes as reagents

Gyöngyvér Kovács, Krisztina Tóth, Zoltán Dinya, László Somsák, Károly Micskei

Research output: Contribution to journalArticle

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Abstract

Reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (3) with chromium(II)L complexes (L = EDTA, NTA, IDA, GLY, MAL) in neutral (5 <pH <7) aqueous DMF gave 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1- enitol (13) in 70-90% yields and > 95% purity. Complexes of Cr(II) with L = EDTA, NTA were similarly efficient with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl chloride (2) in furnishing glucal 13, while with L = IDA, GLY, MAL hydrolysis of 2 could not be suppressed. Under the same conditions [Cr(II)(EDTA)]2- also efficiently gave the corresponding glycals 14-19 from 2,3,4,6-tetra-O-benzoyl- (4) and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (5), per-O-acetylated α-D-galactopyranosyl chloride (6) and bromide (7), α-D-mannopyranosyl chloride (8), α-D-xylopyranosyl chloride (9), and bromide (10), β-D-arabinopyranosyl bromide (11), and α-L-rhamnopyranosyl chloride (12).

Original languageEnglish
Pages (from-to)5253-5264
Number of pages12
JournalTetrahedron
Volume55
Issue number16
DOIs
Publication statusPublished - Apr 16 1999

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Chromium
Bromides
Chlorides
Edetic Acid
Calcium Gluconate
Hydrolysis

Keywords

  • Carbohydrates
  • Chromium compounds
  • Complexes
  • Glycals

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Preparation of acylated pyranoid glycals in neutral aqueous medium by using chromium(II) complexes as reagents. / Kovács, Gyöngyvér; Tóth, Krisztina; Dinya, Zoltán; Somsák, László; Micskei, Károly.

In: Tetrahedron, Vol. 55, No. 16, 16.04.1999, p. 5253-5264.

Research output: Contribution to journalArticle

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AU - Micskei, Károly

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