Dhavale Dilip D, Markad Shankar D, Karanjule Narayan S, PrakashaReddy J
Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India.
J Org Chem. 2004 Jul 9;69(14):4760-6. doi: 10.1021/jo049509t.
The asymmetric dihydroxylation of a d-glucose derived alpha,beta-unsaturated ester 3 afforded syn vicinal diols in good to high diastereoselectivity. The conversion of these vicinal diols to the corresponding cyclic sulfate, regio-, stereoselective nucleophilic ring opening by sodium azide, and LAH reduction afforded amino heptitols 7a,b that were converted to azepane 1c,d and nojirimycin analogues 2c,d.
由d-葡萄糖衍生的α,β-不饱和酯3的不对称双羟基化反应以良好至高的非对映选择性得到顺式邻二醇。这些邻二醇转化为相应的环状硫酸酯，通过叠氮化钠进行区域和立体选择性亲核开环反应，然后经LAH还原得到氨基庚糖醇7a,b，其再转化为氮杂环庚烷1c,d和去氧野尻霉素类似物2c,d。
