Chem. J. Chinese Universities ›› 1996, Vol. 17 ›› Issue (3): 409.

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Studies on Racemization in Thioester Condensation

WANG Hong, JI Hong, ZHANG Ruo-Heng, XU Xiao-Jie, TANG You-Qi   

  1. Institute of Physical Chemistry, Peking University, Beijing, Peking University, Beijing 100871
  • Received:1995-03-16 Online:1996-03-24 Published:1996-03-24

Abstract: In order to study the racemization in thioester condensation,a model coupling reaction between Boc-Ala-Ala-SCH2CH2CO-GlyOBzl and GlyOBzl·TosOHwas monitored by RP-HPLC.To optimize reaction conditions,the effects of solvents,additives and bases were checked.From the results, we conclude that THFis recommendable as a solvent and when thioester:HOsu:NMMis 1:15:12(molar ratio),there is the least racemization(<2%).

Key words: Thioester condensation reaction, RP-HPLC, Racemization ratio

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