Abstract
A neoglycolipid of structure β- D-Glcp-S -( CH 2) 3 N( OH)( CH 2) 4-O- cholest-5- en-3β- yl has been prepared in fair overall yield by reduction of the nitrone obtained by condensation of β- D-Glcp-S-(CH 2) 3NHOH and OCH-( CH 2) 3-O- cholest-5- en-3б- yl . This synthetic procedure is very flexible, allowing a large range of lengths for the spacer arm, different positions for the NOH group along the spacer arm chain and the replacement of the sulfur by other bio-isosteric groups. The new neoglycolipid spontaneously oxidized to the corresponding nitroxide free radical whose EPR spectrum gave information on its conformational equilibrium which was further studied by molecular mechanics.
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