Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses
Institute of Organic Chemistry, University of Tuebingen, Auf der Morgenstelle 18, 72076 Tuebingen, Germany
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Molbank 2020, 2020(1), M1108; https://doi.org/10.3390/M1108
Received: 11 December 2019 / Revised: 8 January 2020 / Accepted: 9 January 2020 / Published: 14 January 2020
(This article belongs to the Special Issue Molecules from Side Reactions)
During the synthesis of symmetrical dodeco-6,7-diuloses that are potential candidates for inhibition of glycosidases, an unanticipated epoxide-oxetane rearrangement was observed. A bicyclic sugar consisting of a glycal moiety and an anomeric esterified furanose was oxidized under epoxidation conditions (mCPBA/KF). The isolation of the pure epoxide was not possible since a rapid reversible conversion accompanied by the migration of the ester group took place and resulted in the formation of an unusual oxetane-bridged disaccharide scaffold. X-ray diffractometric structure elucidation and the suggested mechanism of the rearrangement are provided.
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Keywords:
oxetane; epoxide; rearrangement; carbohydrate; C-glycosylation; spiro-oxetane; ester group migration
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Bayer, M.; Maichle-Mössmer, C.; Ziegler, T. Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses. Molbank 2020, 2020, M1108.
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