Synthesis of new anhydro and branched-chain cyclitols

Zoltán G. Tóth, István F. Pelyvás, C. Szegedi, Péter Benke, Erika Magyar, Tünde Miklovicz, G. Batta, F. Sztaricskai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Starting from D-glucose and D-(-)-quinic acid (5) (1S,5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol (3), and the structurally related α,β-unsaturated alcohols 7 and 8, respectively, were prepared. They have been transformed, by treatment with 3-chloroperoxybenzoic acid, into (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexane- 1-ol (4) and the two diastereoisomeric 4,5-isopropylidenedioxycyclohexane-1-ols 9 and 10. Thermal Claisen rearrangement of the allylic alcohols 3, 7 and 8 resulted in the functionalized branched-chain cyclohexenyl acetamides 12, 13 and 14, respectively. The prepared new cyclitols are useful starting materials for further derivatization to obtain novel enzyme-inhibitors, including phosphorylated cyclitols with 'second-messenger' properties.

Original languageEnglish
Pages (from-to)183-189
Number of pages7
JournalCarbohydrate Research
Volume300
Issue number2
DOIs
Publication statusPublished - May 12 1997

Fingerprint

Cyclitols
Acetamides
Quinic Acid
Second Messenger Systems
Enzyme Inhibitors
Hot Temperature
Alcohols
Glucose

Keywords

  • Cyclitols
  • Enzyme inhibitors

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of new anhydro and branched-chain cyclitols. / Tóth, Zoltán G.; Pelyvás, István F.; Szegedi, C.; Benke, Péter; Magyar, Erika; Miklovicz, Tünde; Batta, G.; Sztaricskai, F.

In: Carbohydrate Research, Vol. 300, No. 2, 12.05.1997, p. 183-189.

Research output: Contribution to journalArticle

Tóth ZG, Pelyvás IF, Szegedi C, Benke P, Magyar E, Miklovicz T et al. Synthesis of new anhydro and branched-chain cyclitols. Carbohydrate Research. 1997 May 12;300(2):183-189. https://doi.org/10.1016/S0008-6215(97)00021-9
Tóth, Zoltán G. ; Pelyvás, István F. ; Szegedi, C. ; Benke, Péter ; Magyar, Erika ; Miklovicz, Tünde ; Batta, G. ; Sztaricskai, F. / Synthesis of new anhydro and branched-chain cyclitols. In: Carbohydrate Research. 1997 ; Vol. 300, No. 2. pp. 183-189.
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