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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 35, Number 3
JKCSEZ 35(3)
June 20, 1991 

Synthetic Studies on Phospholipid Derivatives 1. Comparative Syntheses of (R)-and (S)-Glycerol Acetonide

Phospholipid 유도체에 관한 연구 1. (R)-과 (S)-Glycerol acetonide의 효과적인 비교합성
Sung Ki Chung, B. E. Kim, K. S. Chang

정성기, 김병억, 장기석
천연물질과 합성물질의 전합성에 중요한 중간체인 광학활성의 glycerol acetonide,fmf L-serine, L- and D-ascorbic acid, D-mannitol로부터 합성하였다. 각각의 출발물질로부터 얻어진 (R)-, (S)-glycerol acetonide를 광학적 순도와 수율 {(S)-glycerol : D-mannitol[α]D22 = +15.2˚(34%), D-isoascorbic acid [α]D22 = +14.7˚(28%), (R)-glycerol : L-serine[α]D22 = -12.21˚(26%), L-ascorbic acid [α]D22 = -11.7˚(17%)}을 비교 검토하였다.

The optically active glycerol acetonides are often used as important chiral intermediates for many syntheses. In connection with the development of inhibitors of phospholipases, we have compared the synthetic routes to (S)-and (R)-glycerol acetonide from D-mannitol and D-isoascorbic acid, and L-serine and L-ascorbic acid, respectively. In our hands, the conversions of L-serine to (R)-glycerol acetonide and of D-mannitol to (S)-glycerol acetonide were found to be most effective.

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