(1S,2R,3S,4R)-2,3-O-isopropylidene-4-amino-cyclopentane-1,2,3-triol was prepared from D-alanine by the reaction of esterification, protection of amine group, hydroxylamination of ester group, oxidation of hydroxylamine group and Diels-Alder cycloaddition, dihydroxylation of double bond, protection of hydroxyl group, and de-acyl group and hydrogenation. The reaction conditions of key steps such as hydroxylamination of ester group, oxidation of hydroxylamine and Diels-Alder cycloaddition, dihydroxylation of double bond, and de-acyl group were optimized. The results are as follows: 1) The yield of compoundⅤwas increased from 55% to 90% by using ester Ⅳ instead of N-Boc-alanine as raw maerial; 2) The yield of compound Ⅵ was increased from 53% to 83% by using "one pot" Swern oxidation and the cycloaddition reactions; 3) In the oxidation of double bond, potassium permanganate was used as oxidant instead of highly toxic osmium tetroxide; it avoided using expensive and poisonous reagents. The total yield of the target was 59%, which was increased by 32% compared with the yield in the literature.