Silyl ether deprotection and then selective cleavage of the methyl ester

August 16, 2024

• Title:       

  Silyl ether deprotection and then selective cleavage of the methyl ester

• Image Source:

  Design, synthesis, and biological properties of highly potent tubulysin D analogues

• Mark:

  Scheme 2

• Associated context:

  Silyl ether deprotection and then selective cleavage of the methyl ester over the reactive O-acyl N, O-acetal with  Bu3SnOH provided acid 16 (Scheme 2). Activation of the carboxylic acid as the pentafluorophenyl ester followed by addition of tubuphenylalanine hydrochloride (17) and acetylation of the Tuv alcohol afforded analogue 8.