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

Markus Häner; Christian Herrstedt Hammelev; Christian Marcus Pedersen

doi:10.1002/ejoc.201801094

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

Markus Häner, Christian Herrstedt Hammelev, Christian Marcus Pedersen

Department of Chemistry

Abstract

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.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	40
Pages (from-to)	5532-5537
Number of pages	6
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201801094
Publication status	Published - 1 Nov 2018

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title = "Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives",

abstract = "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.",

author = "Markus H{\"a}ner and {Herrstedt Hammelev}, Christian and Pedersen, {Christian Marcus}",

year = "2018",

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doi = "10.1002/ejoc.201801094",

language = "English",

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pages = "5532--5537",

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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 -

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

Abstract

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