Sharma A, Chattopadhyay S
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai, India.
Enantiomer. 2000;5(2):175-9.
The first enantioselective synthesis of the title compound, (3R)-3-amino-5-methyl-2-oxo-hexan-1-ol hydrochloride (9a), an inhibitor of metalloprotein aminopeptidases has been developed from an enantiomerically pure 3-alkylglycerol. The required 3-alkylglycerol was, in turn, prepared by simple Grignard addition to cyclohexylideneglyceraldehyde 1 followed by separation of the epimeric product carbinols by normal column chromatography. The other attractive features of the synthesis was the use of inexpensive reagents and operationally simple synthetic protocols.
已从对映体纯的3-烷基甘油出发，首次实现了标题化合物（3R）-3-氨基-5-甲基-2-氧代己醇盐酸盐（9a）的对映选择性合成，该化合物是一种金属蛋白氨基肽酶抑制剂。所需的3-烷基甘油则通过格氏试剂简单加成到环己叉甘油醛1上制备，然后通过常规柱色谱法分离差向异构产物甲醇。该合成方法的其他吸引人之处在于使用了廉价的试剂和操作简单的合成方案。
