- Synthesis method of biotin intermediate
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The invention belongs to the field of chemical synthesis of medicines, and particularly discloses a synthesis method of a biotin intermediate 5-((3aS, 6aR)-1, 3-dibenzyl-4-hydroxy-2-oxohexyl-1H-furo [3, 4-d] imidazole-4-yl)-5-olefine acid. The preparation
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Paragraph 0095-0151
(2019/12/29)
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- Synthetic studies on d-biotin. Part 7: A practical asymmetric total synthesis of d-biotin via enantioselective reduction of meso-cyclic imide catalyzed by oxazborolidine
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A novel and convenient method for the stereoselective synthesis of d-biotin 1 starting from the commercially available cis-1,3-dibenzyl-2- imidazolidone-4,5-dicarboxylic acid 2 has been developed. The key features of this synthesis include the enantioselective reduction of a meso-cyclic imide, mediated by a chiral oxazborolidine catalyst, derived from (1S,2S)-(+)-threo-1- (4-nitrophenyl)-2-amino-1,3-propanediol and the direct introduction of a C 5 side chain to the (3aS,6aR)-thiolactone through a modified di-Grignard reaction. Enantioselectivities of 98% in the oxazborolidine- catalyzed asymmetric reduction process have been achieved.
- Chen, Fen-Er,Dai, Hui-Fang,Kuang, Yun-Yan,Jia, Hui-Qing
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p. 3667 - 3672
(2007/10/03)
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