SYNTHESIS OF STREPTOCOCCI PHOSPHATIDYL-α-DIGLUCOSYLDIGLYCERIDE AND RELATED GLYCOLIPIDS. APPLICATION OF THE TETRAISOPROPYLDISILOXANE-1,3-DIYL (TIPS) PROTECTING GROUP IN SUGAR CHEMISTRY. PART V

Article abstract of DOI:10.1016/S0040-4020(01)82351-6

A short and convenient synthesis of phosphatidyl-α-diglucosyldiglyceride (i. e. compound 8d) and two related Streptococci glycolipids (i. e. compounds 6a and 6b) will be presented. 4',6'-Tetraisopropyl-disiloxane-1,3-diyl (TIPS) protected α-glucosyl diglyceride (i. e. compound 2) turned out to be a suitable protected precursor.Thus, compound 2 was selectively condensed with glucosyl bromide 3 to afford 4.Removal of the protecting groups from 4 gave glycolipid 6a.The "dynamic" properties of the TIPS protecting group were utilized to convert 4',6'-TIPS protected 4 into 3',4'-TIPS protected derivative 5a.Compound 5a could then be condensed with either a stearoyl fatty acid or a phosphatidyl moiety to give the fully protected derivatives 5c and 8a, respectively.Finally, removal of all the protecting groups from 5c and 8a afforded the glycolipid 6b and glycophospholipid 8d, respectively.