✦ LIBER ✦

Synthesis of the novel mannosidase inhibitors (3R)- and (3S)-3-(hydroxymethyl)swainsonine

✍ Scribed by Erik J. Hembre; William H. Pearson

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 805 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00362-1

No coin nor oath required. For personal study only.

✦ Synopsis

Swainsonine ( ) is an important mannosidase inhibitor that has been examined clinically as an anticancer drug. The preparation of analogs of swainsonine bearing a hydroxymethyl group at C(3), i.e., (3R)-3-(hydroxymethyl)swainsonine [( ), (3R)-HMS] and (3S)-3-(hydroxymethyl)swainsonine [( ), (3S)-HMS] is described. The synthesis of each analog begins with D-ribose, and involves a Claisen rearrangement, a Sharpless osmylation, and a reductive double-cyclization of either an azido mesylate bearing a lactone (i.e. 24 =:~ 11) or an azido epoxide beating a lactone (i.e. 27 ~ 10). Both (3R)-HMS and (3S)-HMS were found to be effective inhibitors of ot-mannosidase from jack bean.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of the No

ChemInform Abstract: Synthesis of the Novel Mannosidase Inhibitors (3R)- and (3S)-3-( Hydroxymethyl)swainsonine.

✍ E. J. HEMBRE; W. H. PEARSON 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 2 views

Synthesis and mannosidase inhibitory act

Synthesis and mannosidase inhibitory activity of 3-benzyloxymethyl analogs of swainsonine

✍ William H Pearson; Luyi Guo 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 98 KB

Swainsonine (3), an inhibitor of Golgi a-mannosidase II, is a clinical candidate for cancer treatment. In order to avoid potential problems arising from its co-inhibition of lysosomal mannosidases, we have synthesized 3-benzyloxymethyl analogs of swainsonine (17 and 18). Initial screening of these n

ChemInform Abstract: Synthesis and Manno

ChemInform Abstract: Synthesis and Mannosidase Inhibitory Activity of 3-Benzyloxymethyl Analogues of Swainsonine.

✍ William H. Pearson; Luyi Guo 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 2 views

Catalytic enantioselective synthesis of

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

✍ Masaharu Ueno; Hidetoshi Kitagawa; Haruro Ishitani; Satoshi Yasuda; Kentaro Hana 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 64 KB

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.

ChemInform Abstract: Derivatives of (2R,

ChemInform Abstract: Derivatives of (2R,3R,4S)-2-Aminomethylpyrrolidine-3,4-diol are Selective α-Mannosidase Inhibitors.

✍ Florence Popowycz; Sandrine Gerber-Lemaire; Raynald Demange; Eliazar Rodriguez-G 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

Synthesis and α-Mannosidase Inhibitory E

Synthesis and α-Mannosidase Inhibitory Evaluation of (2R,3R,4S)- and (2S,3R,4S)-2-(Aminomethyl)pyrrolidine-3,4-diol Derivatives

✍ Florence Popowycz; Sandrine Gerber-Lemaire; Eliazar Rodriguez-García; Catherine 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 German ⚖ 485 KB 👁 1 views

The synthesis of 46 derivatives of (2R,3R,4S)-2-(aminomethyl)pyrrolidine-3,4-diol is reported (Scheme 1 and Fig. 3), and their inhibitory activities toward a-mannosidases from jack bean (B) and almonds (A) are evaluated (Table ). The most-potent inhibitors are (2R,3R,4S)-2-{[([1,1'-biphenyl]-4-ylmet