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Perhydroxylated 1,7‐Dioxaspiro[5.5]undecanes (“Spiro Sugars”): Synthesis, Stereochemistry, and Structure
Author(s) -
Bextermöller Raphael,
Redlich Hartmut,
Schnieders Klaus,
Thormählen Sven,
Fröhlich Roland
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981002)37:18<2496::aid-anie2496>3.0.co;2-y
Subject(s) - pyran , stereochemistry , chemistry , crystal structure , organic chemistry
As spiro sugars is an apt way of considering perhydroxylated 1,7‐dioxaspiro[5.5]undecanes–a class of compounds which has not been found in nature up to now. The crystal structure of such a spiroacetal, in which the two pyran rings show the β ‐ D ‐ manno configuration, is depicted. Note that the all‐ trans arrangement of C‐6, C,‐5, O pyr , C spiro , O pyr ′ , C‐5′, and C‐6′ does not allow any of the stereoelectronic effects that are typical of carbohydrates.