Synthesis of Symmetrical Dodeco‐6, 7‐diuloses. Issue 28 (15th June 2020)

• Record Type: Journal Article
• Authors: Bayer, Marius; Stocker, Simon; Maichle‐Mössmer, Cäcilia; Ziegler, Thomas
• Is Part Of: European journal of organic chemistry. Issue 28(2020)
• Page Start: 4347
• Page End: 4360
• Publication Date: 2020-06-15
• Subjects: Diulose -- C‐glycosides -- Grubbs metathesis -- Ramberg–Bäcklund reaction -- Oxidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000615
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Dodeco‐6, 7‐diuloses represent a rare class of sugars and can be considered as anomerically linked di‐hexoses with two hemiacetal functions in the middle. Herein, the synthesis of three symmetrical dodeco‐6, 7‐diuloses ( gluco ‐ gluco, galacto ‐ galacto, manno ‐ manno ) is described. For their preparation four synthetic strategies were pursued, whose mutual key step, the connection of the anomeric centers, is particularly emphasized. Specifically, C–C bond forming methods are employed, such as a Grubbs metathesis, a stannyl glycal homocoupling reaction, a coupling of a sulfinyl glycal with a sugar lactone and a Ramberg–Bäcklund rearrangement. Since the ring closure via hemiacetal formation of the target compounds cannot be predicted, intensive NMR spectroscopic structure elucidation of the diuloses was performed. Abstract : Four different synthetic strategies towards dodeco‐6, 7‐diuloses, which are structurally related to naturally occurring Peltalosa, are presented. Furthermore, detailed NMR spectroscopic investigations of these felxible, bis‐hemiacetalic compounds indicate a tendency to form preferred isomers.