D-rybono-1,4-lakton. Część I. Otrzymywanie i wybrane pochodne

Janusz Madaj , Justyna Samaszko-Fiertek , Rafał Ślusarz , Barbara Dmochowska

Abstract

Sugars are extremely important chiral substrates in organic synthesis. Thanks to the possibility of obtaining them from natural sources, their prices are relatively low which increases their attractiveness. d-Ribono-1,4-lactone is included in these compounds. For years it has enjoyed great interest as a substrate. In the early 1980’s two review articles were published in reputable journals [4, 5]. It has been a long time since these articles were published so we have decided to prepare a more up- -to-date review article in Polish. d-Ribono-1,4-lactone can be synthesized in many ways. The most interesting way seems to be the oxidation with KMnO4 [9] or molecular Br2 [10]. The use of bromine may appear to be harmful to the environment. That is why the search for more environmentally friendly methods is ongoing. However, the new methods are not as sufficiently satisfactory and often more expensive than the conventional, previously named methods. Therefore, the most commonly used method is the oxidation of D-ribose with molecular bromine. Very important derivatives of d-ribonolactone are acetal derivatives: 2,3-O-isopropylidene [10, 16] and 3,4-O-benzylidene derivatives [17]. They are often the starting materials for further synthesis. In the case of the latter compound the proper structure was determined by crystallography many years after its synthesis [18]. Very important group of derivatives are derivatives modificated at C-5: sulphonic [21], fluorine [22], chlorine [23], bromine [16, 24], azide [25] and phosphate [27]. Especially important are 5-bromo-5-deoxy derivatives. Examples of their use for the synthesis of thioalditols and thiosugars are described in the literature. It is also worth mentioning the possibility of synthesis of 1,2-unsaturated [ 28–30] and 2,3-unsaturated [31] derivatives. Presented examples of derivatives prove that using a d-ribono-1,4-lactone a whole range of derivatives extremely useful for further synthesis of more complex compounds can be obtained.
Author Janusz Madaj (FCh / DOCh / LCCh)
Janusz Madaj,,
- Laboratory of Carbohydrate Chemistry
, Justyna Samaszko-Fiertek (FCh / DOCh / LCCh)
Justyna Samaszko-Fiertek,,
- Laboratory of Carbohydrate Chemistry
, Rafał Ślusarz (FCh / DOCh / LCCh)
Rafał Ślusarz,,
- Laboratory of Carbohydrate Chemistry
, Barbara Dmochowska (FCh / DOCh / LCCh)
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
Other language title versionsD-ribono-1,4-lactone. Part I. Preparation and selected derivatives
Journal seriesWiadomości Chemiczne, ISSN 0043-5104, e-ISSN 2300-0295, (B 7 pkt)
Issue year2017
Vol71
No11-12
Pages843-859
Publication size in sheets0.8
Keywords in PolishD-rybono-1,4-lakton, otrzymywanie, wybrane pochodne
Keywords in EnglishD-ribono-1,4-lactone, preparation, seleced derivatives
URL http://www.dbc.wroc.pl/dlibra/docmetadata?id=39719
Languagepl polski
LicenseOther; published final; Other open licence; with publication
Score (nominal)7
ScoreMinisterial score = 7.0, 26-02-2018, ArticleFromJournal
Ministerial score (2013-2016) = 7.0, 26-02-2018, ArticleFromJournal
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