Stereoselective Synthesis of 2-Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor
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- 作者：Alex de la Fuente ; Ruben Martin ; Teresa Mena-Barrag谩n ; Xavier Verdaguer ; Jos茅 M. Garc铆a Fern谩ndez ; Carmen Ortiz Mellet ; Antoni Riera
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：July 19, 2013
- 年：2013
- 卷：15
- 期：14
- 页码：3638-3641
- 全文大小：249K
- 年卷期：v.15,no.14(July 19, 2013)
- ISSN：1523-7052
文摘
A practical synthesis of the previously unreported N-acetyl-d-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger 尾-N-acetylglucosaminidase (human placenta) competitive inhibitor than the d-gluco (DNJNAc) and d-galacto (DGJNAc) stereoisomers.