A synthesis of l-ristosamine and a derivative of its C-4 epimer

Ferenc Sztaricskai, István Pelyvás, László Szilágyi, Rezsö Bognár, József Tamás, András Neszmélyi

Research output: Contribution to journalArticle

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Abstract

A synthesis of l-ristosamine from l-rhamnal is described, involving the sequence of reactions: methoxymercuration, tosylation, azide displacement, and reduction, which gave methyl α-l-ristosaminide (10). Acid hydrolysis then afforded l-ristosamine hydrochloride. Trifluoroacetylation of the hydrochloride of 10 followed by saponification and oxidation with ruthenium tetraoxide gave methyl 2,3,6-tri-deoxy-3-trifluoroacetamido-α-l-erythro-hexopyranosid-4-ulose (17). Borohydride reduction of 17 gave a separable, 1:1 mixture of methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-l-ribo- and α-l-xylo-hexopyranoside.

Original languageEnglish
Pages (from-to)193-200
Number of pages8
JournalCarbohydrate Research
Volume65
Issue number2
DOIs
Publication statusPublished - 1978

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Saponification
Derivatives
Borohydrides
Azides
Hydrolysis
Oxidation
Acids
ristosamine
ruthenium tetraoxide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Sztaricskai, F., Pelyvás, I., Szilágyi, L., Bognár, R., Tamás, J., & Neszmélyi, A. (1978). A synthesis of l-ristosamine and a derivative of its C-4 epimer. Carbohydrate Research, 65(2), 193-200. https://doi.org/10.1016/S0008-6215(00)84310-4

A synthesis of l-ristosamine and a derivative of its C-4 epimer. / Sztaricskai, Ferenc; Pelyvás, István; Szilágyi, László; Bognár, Rezsö; Tamás, József; Neszmélyi, András.

In: Carbohydrate Research, Vol. 65, No. 2, 1978, p. 193-200.

Research output: Contribution to journalArticle

Sztaricskai, F, Pelyvás, I, Szilágyi, L, Bognár, R, Tamás, J & Neszmélyi, A 1978, 'A synthesis of l-ristosamine and a derivative of its C-4 epimer', Carbohydrate Research, vol. 65, no. 2, pp. 193-200. https://doi.org/10.1016/S0008-6215(00)84310-4
Sztaricskai, Ferenc ; Pelyvás, István ; Szilágyi, László ; Bognár, Rezsö ; Tamás, József ; Neszmélyi, András. / A synthesis of l-ristosamine and a derivative of its C-4 epimer. In: Carbohydrate Research. 1978 ; Vol. 65, No. 2. pp. 193-200.
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