Next Article in Journal
Dimethyl 2-{[2-(2-Methoxy-1-methoxycarbonyl-2-oxoethyl)-4,5,7-trimethoxy-3-(2,4,5-trimethoxyphenyl)-2,3-dihydro-1H-inden-1-yl]methyl}malonate
Next Article in Special Issue
Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block
Previous Article in Journal
2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol
Previous Article in Special Issue
N′-Acetyl-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine-4-carbohydrazide
Communication

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
*
Author to whom correspondence should be addressed.
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. View Full-Text
Keywords: oxetane; epoxide; rearrangement; carbohydrate; C-glycosylation; spiro-oxetane; ester group migration oxetane; epoxide; rearrangement; carbohydrate; C-glycosylation; spiro-oxetane; ester group migration
Show Figures

Graphical abstract

MDPI and ACS Style

Bayer, M.; Maichle-Mössmer, C.; Ziegler, T. Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses. Molbank 2020, 2020, M1108. https://doi.org/10.3390/M1108

AMA Style

Bayer M, Maichle-Mössmer C, Ziegler T. Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses. Molbank. 2020; 2020(1):M1108. https://doi.org/10.3390/M1108

Chicago/Turabian Style

Bayer, Marius, Cäcilia Maichle-Mössmer, and Thomas Ziegler. 2020. "Unexpected Formation of Oxetanes during the Synthesis of Dodeco-6,7-diuloses" Molbank 2020, no. 1: M1108. https://doi.org/10.3390/M1108

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop