Open Access2‐Propynyl 2,3,4,6‐tetra‐ O ‐acetyl‐α‐ d ‐mannopyranoside
Author(s) -
AlMughaid Hussein,
Robertson Katherine N.,
WernerZwanziger Ulrike,
Lumsden Michael D.,
Cameron T. Stanley,
Grindley T. Bruce
Publication year - 2011
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s010827011005225x
Subject(s) - pyranose , chemistry , propynyl , stereochemistry , ring (chemistry) , tetra , position (finance) , group (periodic table) , cyclohexane conformation , medicinal chemistry , molecule , hydrogen bond , organic chemistry , finance , economics
The 2‐propynyl group in the title compound, C 17 H 22 O 10 , adopts an exoanomeric conformation, with the acetylenic group gauche with respect to position C1. Comparison of 13 C NMR chemical shifts from solution and the solid state suggest that the acetylenic group also adopts a conformation anti to C1 in solution. The pyranose ring adopts a 4 C 1 conformation. Of the three secondary O ‐acetyl groups, that on position O4, flanked by two equatorial groups, adopts a syn conformation, in agreement with recent generalizations [González‐Outeiriño, Nasser & Anderson (2005). J. Org. Chem. 70 , 2486–2493]. The acetyl group on position O3 adopts a gauche conformation, also in agreement with the recent generalizations, but that on position O2 adopts a syn conformation, not in agreement with the recent generalizations.