Premium
Synthesis of Symmetrical Dodeco‐6,7‐diuloses
Author(s) -
Bayer Marius,
Stocker Simon,
MaichleMössmer Cäcilia,
Ziegler Thomas
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000615
Subject(s) - chemistry , glycal , hemiacetal , stereochemistry , anomer , ring (chemistry) , metathesis , lactone , combinatorial chemistry , stereoselectivity , organic chemistry , catalysis , polymer , polymerization
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.