Tethered Glycoderivatives with Unsaturated Spacer: Synthesis and Characterization

Abstract

Williamson coupling of diisopropylidenated monosaccharides with trans-1,4-dibromo-2-butene gave five butenylene-bridged glycoderivatives. Their spectroscopic characterization includes infrared, mass, ¹H and ¹³C NMR, correlation spectrometry, and heteronuclear multiple bond and quantum correlation measurements. This work is part of our effort to obtain chiral building blocks for the synthesis of bolaform and gemini-type surfactants with enhanced biodegradability and biocompatibility.

GRAPHICAL ABSTRACT

Keywords:

• Bolaform
• gemini
• monosaccharide
• tether
• trans-1,4-dibromo-2-butene

Notes

^a Atom numbering is given in Fig. 1.

^a Atom numbering is given in Fig. 1.

^a Atom numbering is given in Fig. 1.