O-GLYCOSIDE TYPE GLYCOLIPID WITH SERINE LONG CHAIN ALKYL DERIVATIVE AS HYDROPHOBIC DOMAIN

摘要

PURPOSE:To provide the subject new compound useful as a material for organic thin films or liposome, having amphiphaticity comparable to those of natural analogues, also high in the thermal stability of the films therefrom in the form of solid phase, significantly highly pure compared to natural analogues, and capable of mass production from inexpensive materials. CONSTITUTION:The objective compound of formula I (S is aldose residue with the reduced terminal carbon involved in o-glycoside linkage; R and R' are each 12-18C alkyl), e.g. N-tetradecanoyl-o-(beta-D-glucopyranoside)-L-serine-dodecyl ester. The compound of the formula I can be obtained by reaction of a serine long chain alkyl derivative of formula II with 1 to 3 molar times of a reduced terminal-activated sugar chain component of formula Z-Y (Z is aldose residue with all of the hydroxyl groups except the reduced terminal one protected by acetyl groups; Y is active group for the o-glycoside linkage formation at the reduced terminal) to form an o-glycoside linkage followed by eliminating the acetyl groups as the protecting groups for the sugar chain components.