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Search for "aminocyclitols" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

  • Emine Salamci and
  • Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

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  • -azido-3,8-bis(benzyloxy)cyclooctyl methanesulfonate with Zn/NH4Cl and debenzylation resulted in the target aziridinecyclooctanediol. Keywords: aminocyclitols; aminocyclooctanetriol; azides; aziridines; aziridinecyclooctanediol; Introduction Aziridines are the smallest nitrogen-containing heterocycles
  • ]. Furthermore, aziridine derivatives are valuable precursors for the synthesis of aminocyclitols, which can be found in nature in several families of natural and clinically important antibiotics [10]. Aminocyclitols containing the amino alcohol motif are important structural components for modifying bioactive
  • natural products and pharmaceuticals. Valienamine (3) and its analogues show inhibitory activity against certain glycosidases [11][12][13] (Figure 1). Many groups have described different synthetic methods for the synthesis of various aminocyclitols [13][14][15][16][17]. However, only few synthetic
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Published 11 Nov 2022

Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

  • İlknur Polat,
  • Selçuk Eşsiz,
  • Uğur Bozkaya and
  • Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

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  • . We have recently reported the synthesis of various eight-membered aminocyclitols and their derivatives [19][20][21][22][23][24][25]. In the present paper, we describe the synthesis of some hydroxylated β-amino acid derivatives containing eight-membered rings starting from cis,cis-1,3-cyclooctadiene
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Published 06 Jan 2022

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

  • Emine Salamci and
  • Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

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  • stereospecifically new chlorocyclooctanetriols. Keywords: aminocyclitols; aminocyclooctanetriol; chlorocyclooctanetriol; cyclic sulfate; cyclitols; Introduction The synthesis of aminocyclitols has attracted attention because they contain substructures of many biologically active natural products [1][2][3]. They
  • have become important structural components for drug development with a modifying action as inhibitors of glycosidases [4][5][6][7][8][9][10]. Aminocyclitols are amino polyhydroxy cycloalkanes [2] formally derived from cyclitols [11][12][13][14][15], which are polyhydroxylated cycloalkanes, via
  • replacement of one of the hydroxy groups with an amino group. Many aminocyclitols and their derivatives have been found to possess antibiotic properties, such as validamycins (1) [16]. Validamycin A (1) contains two aminocyclitol units, the one is valienamine (2) and the other is validamine (3, Figure 1). One
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Published 11 Mar 2021

Regio- and stereoselective synthesis of new diaminocyclopentanols

  • Evgeni A. Larin,
  • Valeri S. Kochubei and
  • Yuri M. Atroshchenko

Beilstein J. Org. Chem. 2014, 10, 2513–2520, doi:10.3762/bjoc.10.262

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  • those mimics may subtly influence their biological activity [11][12][13][14]. The functionalization of synthetic, unnatural aminocyclitols represents an attractive strategy towards the preparation of aminoglycoside and nucleoside mimics, and the development of common synthesis routes to various regio
  • subsequent oxirane ring opening represent a viable approach for the development of new pharmaceutically relevant scaffolds. As a part of our ongoing research in the development of new aminocyclitols, we exploited cyclopentane derivatives to mimic both the 2-deoxystreptamine ring, a core component in
  • with hydrogen bond donors [25]. Additionally, the synthesis of aminocyclitols from cyclitol epoxides has been described [26][27]. It has been shown that the reaction of cyclitol epoxides with nitrogen-containing nucleophiles in the presence of Lewis acids gave a mixture of C1 and C2 adducts. Both
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Published 28 Oct 2014

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

  • Latif Kelebekli,
  • Yunus Kara and
  • Murat Celik

Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15

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  • KMnO4 or OsO4 followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols. Keywords: aminocyclitol; cyclitols; endoperoxide
  • ring resembles the configuration of conduramine D-2 [31][40][41]. The cyclic polyhdroxylated amines, also known as aminocyclitols, possess a wide variety of biological activities [42][43][44][45]. In conclusion, we have outlined the synthesis of a new family of aminocyclitols analogues 6 and 7 based on
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Published 15 Feb 2010

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

  • Olivia Andriuzzi,
  • Christine Gravier-Pelletier,
  • Gildas Bertho,
  • Thierry Prangé and
  • Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

Graphical Abstract
  • Diastabol®, Basen® and Glucor® or Precose®). Results In that context, new C8-carbasugars and related aminocyclitols have been targeted in order to study the effect of the enhanced flexibility and of the new spatial distribution displayed by these structures on their adaptability in the active site of the
  • new eight-membered carbasugars (Figure 2, A = OH) and related aminocyclitols (A = NHR) from C2-symmetrical L-ido- or D-manno- cyclooctene, easily available by ring closing metathesis of 1,9-diene derived from L-ido- or D-manno-bis-epoxide [33]. Thus, synthetic potentialities of the newly created
  • aminocyclitols it could be an epoxidation followed by the nucleophilic opening of the epoxide moiety by a primary amine or another nitrogen nucleophile. Accordingly (Scheme 1), treatment of the fully O-protected L-ido-cyclooctene 1 with a 5 mol% aqueous solution of osmium(IV) tetroxide [34] in acetone in the
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Published 07 Oct 2005
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