The application relates to the technical field of
organic synthesis and pharmaceutical intermediates, in particular to a (2S, 4R)-1-Fmoc-4-(O-allyloxycarbonylmethyl)-
proline and a synthesis method thereof. The method comprises the following steps: performing
silicon-based protection on (2S, 4R)-4-hydroxypyrrolidine-2-
carboxylic acid; refluxing and dehydrating the
alkyl aldehyde to construct a tetrahydropyrrolooxazolone bicyclic intermediate; after the
silicon-based group is removed, etherification is performed with 2-haloacetic acid allyl ester under strong alkali to introduce a
side chain; and finally, acid ring-opening
hydrolysis and Fmoc protection are performed to obtain the target product. The amino group and the carboxyl group are protected in situ by constructing a bicyclic structure, the sensitive allyloxycarbonylmethyl
side chain is introduced in a non-water
system, and the
hydrolysis of the
side chain ester bond is effectively avoided. The product prepared by the application has high purity and good
stereoselectivity, and an efficient and low-cost industrialization approach is provided for the synthesis of high-performance polypeptide blocks.