P.M.R. Studies of some open-chain derivatives obtained from L-arabinose and L-cysteine

Lázló Szilágyi, Z. Györgydeák

Research output: Contribution to journalArticle

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Abstract

Accurate p.m.r. parameters for methyl 2(R)- and 2(S)-(L-arabino-1,2,3,4-tetra-acetoxybutyl)thiazolidine-4(R)-carboxylate (1 and 2), 3-acetyl-2(R)-(L-arabino-2,3,4- triacetoxy-1-hydroxybutyl)thiazolidine-4(R)-carboxylic acid 4,l'-lactone (3), and N,N-dimethyl-3-acetyl-2(R)-(L-arabino-2,3,4-triacetoxy-1-hydroxybutyl)thiazolidine-4(R)-carboxamide (4) were obtained by computer-assisted analysis of their spectra. The polyacetoxyalkyl side-chain was shown to possess a planar zig-zag conformation in each compound, although some distortions occurred in 3 and 4. The configurations at C-2 in the diastereoisomers 1 and 2 were ascertained on the basis of the JNH.CH coupling-constants.

Original languageEnglish
Pages (from-to)159-169
Number of pages11
JournalCarbohydrate Research
Volume48
Issue number2
DOIs
Publication statusPublished - 1976

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Thiazolidines
Arabinose
Cysteine
Derivatives
Lactones
Spectrum Analysis
Carboxylic Acids
Conformations
thiazolidine-4-carboxylic acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

P.M.R. Studies of some open-chain derivatives obtained from L-arabinose and L-cysteine. / Szilágyi, Lázló; Györgydeák, Z.

In: Carbohydrate Research, Vol. 48, No. 2, 1976, p. 159-169.

Research output: Contribution to journalArticle

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AB - Accurate p.m.r. parameters for methyl 2(R)- and 2(S)-(L-arabino-1,2,3,4-tetra-acetoxybutyl)thiazolidine-4(R)-carboxylate (1 and 2), 3-acetyl-2(R)-(L-arabino-2,3,4- triacetoxy-1-hydroxybutyl)thiazolidine-4(R)-carboxylic acid 4,l'-lactone (3), and N,N-dimethyl-3-acetyl-2(R)-(L-arabino-2,3,4-triacetoxy-1-hydroxybutyl)thiazolidine-4(R)-carboxamide (4) were obtained by computer-assisted analysis of their spectra. The polyacetoxyalkyl side-chain was shown to possess a planar zig-zag conformation in each compound, although some distortions occurred in 3 and 4. The configurations at C-2 in the diastereoisomers 1 and 2 were ascertained on the basis of the JNH.CH coupling-constants.

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