Remarkable Stereoselectivity in the Inhibition of α-Galactosidase from Coffee Bean by a New Polyhydroxypyrrolidine Inhibitor
✍ Scribed by Dr. Yi-Fong Wang; Dr. Yoshikazu Takaoka; Prof. Dr. Chi-Huey Wong
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 397 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0044-8249
No coin nor oath required. For personal study only.
✦ Synopsis
COMMUNICATIONS
(1.3 g. 4.86 mmol). silver triflate (1.5 s. 1.2 equiv. 5.84 mmol). and triethylamine (0.59 g. 1.2 equiv. 5.X4 mmol). The suspension was stirred at -20 C for 4 h and then filtered through a bed of Celite. The filtrate was washed twice with water and twice with saturated sodium bicarbonate. The organic layer uas dried ovcr mhydrous MgSO, and concentrated in wcuo. and the rcsidue u a s chromatographed with silica pcl (eluted with Et0Ac;hex;ine = 6:l (v!v)) topive thedesired product 3a as a white solid (1.9 g. 68% yield). ' H NMR (500 Hz. CDCI,) d = 1.30 (d. J = 6.5 Hz. 3H). 1.91 (s. 3H). 1.9X (s. 3H). 2 01 (s. 3H). 2.02 (s. 3H). 3.77 (s. 3H). 4.00 (m.lH).4.0~(dd.J=2.5.l1.5Hz.1H).4.21(dd.J=6.0.12.5Hz.lH).4.35(dd. J = 2.5. 6.5 Hz. 1H). 4.43 (dd. J = 2.5. 9.5 Hz. 1H). 4.82 (d. J = 1.5 Hz. 1 H). 4.96 (s. 1H). 5.12 (s. 2H). 5.21 (dd. J = 1 . 5 , 4.5Hz. 2H). 5.46 (d. J = 9 . 5 H z . 1H).
7.25 7.32 (m. 5H): ' 3 C ; 1 H ) NMR (CDCI,) d =17.h. 20.4. 20.6. 52 6. 58.3. 62.1. 62.2. 65.9. 67.0. 68.2. 68.3. 69.3.98.5. 127 7