(3aR,6aS)-1,3-二苄基四氢-4H-呋喃并[3,4-d]咪唑-2,4(1H)-二酮的转化利用

Conversion and Utilization of (3aR,6aS)-1,3-Dibenzyl-tetrahydro-4H-furo[3,4-d]imidazol-2,4(1H)-dione

在(+)-生物素的不对称全合成工艺中产生的副产物(3aR,6aS)-1,3-二苄基四氢-4H-呋喃并[3,4-d]咪唑-2,4(1H)-二酮(2),经过开环酯交换、两次氧化和水解即可方便地转化得到合成(+)-生物素的关键中间体顺-1,3-二苄基-4,5-二羧基-2-咪唑烷酮,总收率74%,实现了副产物的循环利用。

cis-1,3-Dibenzyl-4,5-dicarboxy-2-imidazolidone （1）, a key intermediate of （＋）-biotin, was synthesized from （3aR,6aS） - 1,3-dibenzyl-tetrahydro-4H-furo [3,4-d] imidazol-2,4 （1H） -dione （2） by ring-opening / esterification, oxidation at twice and hydrolysis with an overall yield of 74 %. This process realized the utilization of a main by-product 2 in asymmetric synthesis of （＋） -biotin.