78841-89-1Relevant academic research and scientific papers
SYNTHESIS OF STREPTOCOCCI PHOSPHATIDYL-α-DIGLUCOSYLDIGLYCERIDE AND RELATED GLYCOLIPIDS. APPLICATION OF THE TETRAISOPROPYLDISILOXANE-1,3-DIYL (TIPS) PROTECTING GROUP IN SUGAR CHEMISTRY. PART V
Boeckel, C. A. A. van,Boom, J. H. van
, p. 4567 - 4576 (2007/10/02)
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.
SYNTHESIS OF MEMBRANE SUBSTANCES: PHOSPHATIDYL-α-DIGLUCOSYL DIGLYCERIDE AND RELATED GLYCOLIPIDS
Boeckel, Stan A. A. van,Boom, Jacques H. van
, p. 581 - 584 (2007/10/02)
The recently developed tetraisopropyldisiloxane-1,3-diyl protecting group enabled us to synthesize a naturally occurring phosphatidyl-α-diglucosyl diglyceride as well as the glycolipid α-diglycosyl diglyceride and a derivative thereof which is acylated on
