Cleavage of the acetal rings in bis(methyl 4,6-O-benzylidene-α-d-glucopyranosido)-18-crown-6

Péter Bakó, László Fenichel, László Toke, Gábor Tóth

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Treatment of bis(methyl 4,6-O-benzylidene-2,3-dideoxy-α-d-glucopyranosido [2,3-b][2′,3′-k])-1,4,7,10,13,16-hexaoxacyclo-octadecane (1) with aqueous acetic acid gave bis(methyl 2,3-dideoxy-α-d-glucopyranosido[2,3-b][2′,3′-k])-1,4,7,10,13,16-hexaoxacyclo-octadecane (2). With LiAlH4AlCl3, 1 gave a mixture of three O-benzyl derivatives in which bis(methyl 4-O-benzyl-2,3-dideoxy-α-d-glucopyranosido[2,3-b][2′,3′-k])-1,4,7,10,13,16-hexaoxacyclo-octadecane preponderated. Methylation and butylation of 2 in a two-phase system gave the tetramethoxy and tetrabutoxy crowns. Bis(methyl 4-O-acetyl-2,3-dideoxy-6-O-trityl-α-d-glucopyranosido[2,3-b][2′,3′-k])-1,4,7,10,13, 16-hexaoxacyclo-octadecane (5) was obtained from 2 by tritylation and acetylation. Detritylation of 5 with acetic acid-hydrogen bromide gave bis(methyl 4-O-acetyl-2,3-dideoxy-α-d-glucopyranosido[2,3-b][2′,3′-k])-1,4,7,10,13, 16-hexaoxacyclo-octadecane. Treatment of 1 with N-bromosuccinimide gave the 4-benzoyl-6-bromo-6-deoxy compound which was suitable for making a new ring with a trans-annular connection. The complex stability constant of each new crown has been measured and evaluated.

Original languageEnglish
Pages (from-to)31-37
Number of pages7
JournalCarbohydrate Research
Volume147
Issue number1
DOIs
Publication statusPublished - Mar 1 1986

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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