Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

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• 作者：Gé ; raldine Le Bouc ; Christine Thomassigny and Christine Greck
• 刊名：Tetrahedron: Asymmetry
• 出版年：2006
• 出版时间：14 August 2006
• 年：2006
• 卷：17
• 期：13
• 页码：2006-2014
• 全文大小：207 K

文摘

The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-d-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-l-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose—while 3 and 4 were obtained from 1,2:5,6-di-O-isopropylidene-α-d-allofuranose. These compounds were transformed in a few steps to the corresponding β-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting β-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively.