Boydell A James, Jeffery Martin J, Bürkstümmer Eva, Linclau Bruno
Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, UK.
J Org Chem. 2003 Oct 17;68(21):8252-5. doi: 10.1021/jo034374x.
On the basis of our previously described selective protection of arabitol as its 1,2:4,5-bis-pentylidene acetal 5, we report a straightforward synthesis of the novel "pseudo"-C(2)-symmetric 3-azido-1,2:4,5-diepoxypentane building block 4 in 6 steps from arabitol. Using a similar synthetic route, an improved synthesis of the C(2)-symmetrical 1,2:4,5-bis-epoxypentane building block 1 is described, also in 6 steps from arabitol. Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis.
基于我们之前所描述的将阿拉伯糖醇选择性保护为其1,2:4,5-双亚戊基缩醛5的方法，我们报道了一种从阿拉伯糖醇出发，经6步反应直接合成新型“假”C(2)-对称的3-叠氮基-1,2:4,5-二环氧戊烷结构单元4的方法。使用类似的合成路线，还描述了一种从阿拉伯糖醇出发，同样经6步反应对C(2)-对称的1,2:4,5-双环氧戊烷结构单元1的改进合成方法。1和4的两种对映体均可获得，并且所有涉及的反应都易于进行大规模合成。
