Synthesis of Specifically Labelled Ganglioside [1c-13C]-GM3

✍ Scribed by Lutz F. Tietze; Dirk Gretzke

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 324 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199809)1998:9<1895::aid-ejoc1895>3.0.co;2-s

✦ Synopsis

Glycosidation of the lactose derivative 4 with [1-13 C]-sialyl sialic acid gave the trisaccharide 5 which was transformed into [1c-13 C]-GM 3 ([1c-13 C]-1). xanthate 3, prepared from enzymatically obtained [1-13 C]-FULL PAPER Scheme 2 Reagents and conditions: (a) PST, AgOTf, CH 3 CN/CH 2 Cl 2 , Ϫ70°C (42%); (b) (i) Pd(OH) 2 /C, H 2 , MeOH, (ii) Ac 2 O/Py, 0°C (76%); (c) BF 3 иOEt 2 , CH 2 Cl 2 , 0°C (95%); (d) CCl 3 CN, DBU, CH 2 Cl 2 (84%).

moval of the protecting group at C-1a with boron trifluo-with trichloroacetonitrile in the presence of DBU to afford 8 in 84% yield. rideϪdiethyl ether gave 7 in 95% yield [17] . For the glycosidation of azidosphingosine 9, the trisaccharide 7 was trans-Glycosidation of 3-O-benzoylazidosphingosine 9 [19] as acceptor with 8 in the presence of boron trifluorideϪdiethyl formed into the α-trichloroacetimidate [18] 8 by treatment Scheme 3 Reagents and conditions: (a) 9, BF 3 •OEt 2 , 0°C (75%); Lindlar catalyst, H 2 , C 36 H 70 O 3 (76%); (c) (i) NaOMe/MeOH, (ii) H 2 O, (iii) IRA 120 (88%).