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Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate.


ABSTRACT: Optically pure sitagliptin phosphate monohydrate is efficiently and practically synthesized through a chiral hemiacetal as the key intermediate in 54% overall yield starting from (E)-4-(2,4,5-trifluorophenyl)but-2-enal and N-boc-protected hydroxylamine. The chiral hemiacetal fragment is constructed by a tandem aza-Michael/hemiacetal reaction catalyzed by an organocatalyst and the influence of acidity of Brønsted acid on tandem aza-Michael/hemiacetal reaction is researched in detail.

SUBMITTER: Gao H 

PROVIDER: S-EPMC6099835 | biostudies-other | 2018 Jun

REPOSITORIES: biostudies-other

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Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate.

Gao Haoling H   Yu Jiangang J   Ge Chengsheng C   Jiang Qun Q  

Molecules (Basel, Switzerland) 20180613 6


Optically pure sitagliptin phosphate monohydrate is efficiently and practically synthesized through a chiral hemiacetal as the key intermediate in 54% overall yield starting from (<i>E</i>)-4-(2,4,5-trifluorophenyl)but-2-enal and <i>N</i>-boc-protected hydroxylamine. The chiral hemiacetal fragment is constructed by a tandem aza-Michael/hemiacetal reaction catalyzed by an organocatalyst and the influence of acidity of Brønsted acid on tandem aza-Michael/hemiacetal reaction is researched in detail  ...[more]

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