Synthesis of streptococci phosphatidyl-α-diglucosyldiglyceride and related glycolipids : Application of the tetraisopropyldisiloxane-1,3-diyl (tips) protecting group in sugar chemistry. Part V |
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Authors: | CAA van Boeckel JH van Boom |
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Institution: | Gorleus Laboratories, P.O. Box 9502, 2300 RA Liedenthe Netherlands |
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Abstract: | A short and convenient synthesis of phosphatidyl-α-diglucosyldiglyceride (i.e. compound ) and two related Streptococci glycolipids (i.e. compounds and ) will be presented. 4',6'-Tetraisopropyl-disiloxane-1,3-diyl (TIPS) protected α-glucosyl diglyceride (i.e. compound ) turned out to be a suitable protected precursor. Thus, compound was selectively condensed with glucosyl bromide to afford . Removal of the protecting groups from gave glycolipid . The “dynamic” properties of the TIPS pro- tecting group were utilized to convert 4',6'-TIPS protected into 3',4'- TIPS protected derivative . Compound could then be condensed with either a stearoyl fatty acid or a phosphatidyl moiety to give the fully protected derivatives and , respectively. Finally, removal of all the protecting groups from and afforded the glycolipid and glycophospholipid , respectively. |
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