The Journal of organic chemistry

Efficient synthesis of a configurationally stable L-serinal derivative

D Yoo, JS Oh, DW Lee, YG Kim

Index: Yoo, Dongwon; Seok Oh, Joon; Lee, Dong-Whal; Kim, Young Gyu Journal of Organic Chemistry, 2003 , vol. 68, # 7 p. 2979 - 2982

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Citation Number: 27

Abstract

An efficient synthesis of a configurationally stable l-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from l-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.

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