A series of glucopyranose (α-D-glucose, β-D-glucose, D-gluconic acid and 6-amino-6-deoxy-D-glocuse) terminated alkanethiol acetals have been successfully synthesized. α and β-D-glucose were configured in controlled ways coupling with alkanethiol, in which bromosugar and trichloroacetirnidates were selected as activated glycosyl donors using different promoters tetraalkylammonium bromide (Et₄NBr) and trimethylsilanetriflate (TMSOTf) respectively.

The glycosylation of glucuronic acid and 6-amino-6-deoxy-β-D-glucose to ω-mercaptohexadecanol depends on powerful donors and stronger promoters. The corresponding trichloroacetimidates of the methyl D-glucuronic ester and 6-azido-6-deoxy-β-D-glucose were used as active donors, and strong Lewis acid, trimethylsilyl triflate (TMSOTf) was also involved in this study.

These structures were mixed in different proportions with HO(CH₂)₁₆SH, and the corresponding SAMs on gold were characterized by ellipsometry, contact angle goniometry, and infrared reflection-absorption spectroscopy. Infrared reflection­absorption spectroscopy (IRAS) indicated well-ordered SAMs with a high degree of crystallinity on the hydrocarbon layer. Different orientation between α and β-D-glucose self-assembled monolayers, and the functionality of carboxyl acid and amine were explored on surface for further immobilization of lipid bilayers.

New model systems were developed, in which amphiphilic hexadecly OEG derivative or glucose derivatives were designed to present self-assembled monolayers on gold. HS(CH₂)₁₅CONH-EG₆-CH₂CONH(CH₂)₁₅CH₃ displayed particularly sharp features in IRAS spectra at room temperature. Carbohydrate unit instead of OEG moiety could be more natural and it possesses three-dimensional water-filled space.