无保护基合成 2-脱氧氮杂糖。

Malaghan Institute of Medical Research, P.O. Box 7060, Wellington, New Zealand.

Molecules. 2009 Dec 16;14(12):5298-307. doi: 10.3390/molecules14125298.

The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.

1,2,4-三脱氧-1,4-亚氨基-L-山梨醇的无保护基不对称合成可从 2-脱氧-D-核糖经 5 步反应以 48%的总收率轻易实现。该合成的关键是我们最近开发的 Vasella 还原胺化和氨基甲酸酯环合方法在 2-脱氧氮杂糖合成中的应用。氨基甲酸酯环合反应以优异的产率和非对映选择性（>20:1 d.r.，有利于 3,4-顺式异构体）发生。