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. 2016 Nov 16;11:6103–6121. doi: 10.2147/IJN.S112432

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© 2016 Li et al. This work is published and licensed by Dove Medical Press Limited

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Design and synthesis of a novel αGalCer analog PBS-44.

Notes: (a) Ph₃P=CH(CH₂)₁₂CH₃, THF (60%); (b) OsO₄, N-methylmorpholine N-oxide, t-BuOH, H₂O (70% for 3, 28% for 4); (c) HCl, THF; MeOH; HO₂C(CH₂)₁₂CH=CH(CH₂)₇CH_3, dicyclohexylcarbodiimide, N-hydroxysuccinimide, THF, dimethylamino pyridine (47%); (d) sodium methoxide, MeOH; tert-butyldimethylsilyl chloride, imidazole, THF (57%); (e) AC₂O, TFA; HBr, AcOH, methylene chloride (40%); (f) AgOTf, 4Å mol sieves, methylene chloride, H₂, Pd/C, EtOAc, EtOH, sodium methoxide, MeOH (85%).

Abbreviation: αGalCer, α-galactosylceramide.