The oxolane ring opening of some muramic acid derivatives under acidic conditions

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

Abstract

Synthesis of 1,6-anhydro sugars is well known in literature. The dioxolane ring exhibits at least two types of properties. It can be used as a protecting group and reaction site. This work discusses the cleavage of the 1,6-anhydro ring of muramic acid derivatives. To induce the opening of the dioxolane ring in 1,6-anhydro-D-glucose derivatives three types of reagents were used (TFA/Ac2O, Sc(OTf)3/Ac2O, H2SO4/Ac2O). This method is commonly used in sugar chemistry for opening 1,6-anhydro ring. This process led to the preparation of compounds with very good yields (80%, even 98%). In the first attempt the mixture of TFA/Ac2O (1:9) was used. Besides the main product 4, the 3,4-di-Oacetyl- 1,6-anhydro-2-azide-2-deoxy-β-D-glucopyranose was observed as a side product. Main product 4 was obtained as the mixture of α and β (2:1) anomers. Better stereoselectivity was obtained using Sc(OTf)3. In this case, the main product was received with β configuration. The best yield (65%) was obtained using a mixture of H2SO4 and Ac2O and mixture of two anomers of N-acetyl-1,4,6-tri-Oacetyl- 2-deoxy-D-muramic acid ethyl ester was isolated (α and β, 1:4). Depending on which method was used to open dioxolane ring of 1,6-anhydroMur derivative we were able to control the stereochemistry of the reaction and to obtain pure α anomer or mostly β anomer.
Author Justyna Samaszko-Fiertek (FCh / DOCh / LCCh)
Justyna Samaszko-Fiertek,,
- Laboratory of Carbohydrate Chemistry
, Barbara Dmochowska (FCh / DOCh / LCCh)
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
, Rafał Ślusarz (FCh / DOCh / LCCh)
Rafał Ślusarz,,
- Laboratory of Carbohydrate Chemistry
, Janusz Madaj (FCh / DOCh / LCCh)
Janusz Madaj,,
- Laboratory of Carbohydrate Chemistry
Journal seriesLetters in Organic Chemistry, ISSN 1570-1786, (A 15 pkt)
Issue year2018
Vol15
No8
Pages693-697
Publication size in sheets0.5
Keywords in EnglishMur-derivative, 1,6-anhydro derivative, cleavage of 1,6-anhydro linkage, dioxolane ring, TFA/Ac2O, Sc(OTf)3/Ac2O, H2SO4/Ac2O
DOIDOI:10.2174/1570178615666180119152605
Languageen angielski
Score (nominal)15
ScoreMinisterial score = 15.0, 10-11-2018, ArticleFromJournal
Ministerial score (2013-2016) = 15.0, 10-11-2018, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 0.73 (2) - 2016=0.691 (5)
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