Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives

TY - JOUR

T1 - Conformational Distortion Using a Molecular Lever

T2 - Synthesis and Conformational Studies of Galactoside Derivatives

AU - Häner, Markus

AU - Herrstedt Hammelev, Christian

AU - Pedersen, Christian Marcus

PY - 2018/11/1

Y1 - 2018/11/1

N2 - Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.

AB - Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.

U2 - 10.1002/ejoc.201801094

DO - 10.1002/ejoc.201801094

M3 - Journal article

SN - 1434-193X

VL - 2018

SP - 5532

EP - 5537

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 40

ER -