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Catalytic enantioselective synthesis of a novel inhibitor of ceramide trafficking, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12)

✍ Scribed by Masaharu Ueno; Hidetoshi Kitagawa; Haruro Ishitani; Satoshi Yasuda; Kentaro Hanada; Shū Kobayashi

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 64 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01658-6

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✦ Synopsis

CH 2 Cl 2 , -45 ˚C Zr(O t Bu) 4 (10 mol%) (R)-6,6'-Br 2 BINOL (22 mol%) N-methylimidazole (12 mol%) 2 3 MS4A (250 mg/mmol) R = Bn(3a) 39% yield, 54% ee. R = TBDPS(3b) 71% yield, 16% ee. R = TBS(3c) 47% yield, 80% ee.

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