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Influence of an Ethynyl or a Buta‐1,3‐diynyl Group on the Chemical Shifts of Hydroxy Groups of Glucopyranoses
Author(s) -
Bernet Bruno,
Bürli Roland,
Xu Jinwang,
Vasella Andrea
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200206)85:6<1800::aid-hlca1800>3.0.co;2-s
Subject(s) - chemistry , vicinal , chemical shift , group (periodic table) , medicinal chemistry , stereochemistry , organic chemistry
A comparison of the OH chemical shifts for 1‐mono‐, 4‐mono‐, and 1,4‐diethynylated and 1,4‐buta‐1,3‐diynylated glucopyranoses with those of β ‐ D ‐glucopyranose ( 1 ) identified characteristic increments for the OH (downfield) shifts of the alkynylated glucopyranoses in (D 6 )DMSO solution. For ethynylated derivatives, the increments vary from 0.05 ppm for HOC(6) (replacement of HOC(1) by an axial ethynyl group) to 0.5 ppm for HOC(2) (replacement of HOC(1) by an equatorial ethynyl group). The increments for buta‐1,3‐diynylated derivatives are larger, and vary from 0.1 to 0.7 ppm. The influence on the shift for vicinal OH groups is stronger for such a substitution at C(1) rather than at C(4).