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Rational Design and Synthesis of Highly Potent β-Glucocerebrosidase Inhibitors

✍ Scribed by Xiaoxiang Zhu; Kamlesh A. Sheth; Shihong Li; Hui-Hwa Chang; Jian-Qiang Fan

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
114 KB
Volume
117
Category
Article
ISSN
0044-8249

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✦ Synopsis

Scheme 1. Synthesis of IFG (1) and IFG derivatives 2-8. a) CH 2 = C(OMe)Me, TsOH•H 2 O, THF, 1.5 h, 0 8C (53 %); b) Tf 2 O, pyridine, CH 2 Cl 2 , 2 h, À78!0 8C; then KCN, 18[crown]-6, DMF, 16 h, RT (80 %); c) RMgX, Et 2 O, 2 h, RT; then NaBH 4 , overnight, RT (65-74 %); d) H 2 , 20 % Pd(OH) 2 /C, AcOH, MeOH, 50 psi, overnight, RT; then 1 n HCl (52-81 %); e) H 2 , 20 % Pd(OH) 2 /C, HCl (conc.), MeOH, RT (81 %); f) aldehyde, NaBH 3 CN, MeOH (79-83 %). Tf = trifluoromethanesulfonyl.

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