Synthesis and NMR elucidation of four novel
2-(trimethylsilyl)ethyl glycosides
Huanhuan Qu
•
Wenji Sun
•
Yanyan Zhang
•
Matthieu Sollogoub
•
Yongmin Zhang
Received: 22 November 2012 / Accepted: 15 January 2013 / Published online: 3 February 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a
short and efficient route starting from
D
-glucose. Their structures were elucidated by
applying high-resolution mass spectra, and one-dimensional and two-dimensional
NMR techniques. These glycosides were prepared and used as intermediate building
blocks in the scheme developed for oligosaccharide construction.
Keywords Total synthesis Á Structure elucidation Á Glycosides Á NMR
spectroscopy Á Oligosaccharides
Introduction
Over the past three decades or so, carbohydrate chemistry has emerged from a fairly
self-contained and specialized field to one that has been thrust into a position of
center stage in chemical research. This shift in focus for the area, sometimes
referred to as ‘‘glycoscience’’, has arisen through the impact of carbohydrates on
many disciplines: biochemistry, immunology, medicinal chemistry, plant science,
food science, and nanomaterials, to name a few [1]. In recent years, a steadily
increasing research effort has been centered on the production of glycosides, and
particularly of oligo- and polysaccharides. Crucial impetus has come from the
increasing interest shown by biochemists in these substances [2].
H. Qu (&) Á Y. Zhang Á M. Sollogoub Á Y. Zhang
Institut Parisien de Chimie Mole
´
culaire (UMR CNRS 7201), Universite
´
Pierre et Marie Curie-Paris
6, C.181, 4 Place Jussieu, 75005 Paris, France
e-mail: aiby116@163.com
H. Qu Á W. Sun
Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi’an 710069, People’s
Republic of China
123
Res Chem Intermed (2014) 40:1557–1564
DOI 10.1007/s11164-013-1060-0
@Phil_Robichaud
@deepthiw
@JoseServera