201285-54-3

Upstream product

• 4991-65-5 tioxolone 
• 201285-50-9 6-tert-butoxy-1,3-benzoxathiole 
• 201285-48-5 6-tert-butoxy-1,3-benzoxathiol-2-one 

Downstream Products

• 201285-56-5 (S)-N-((S)-1-Carboxy-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-(6-hydroxy-benzo[1,3]oxathiol-5-ylmethyl)-succinamic acid tert-butyl ester 
• 201285-58-7 (S)-N-((S)-1-Carboxy-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-N-(6-hydroxy-3-oxo-2,3-dihydro-3λ⁴-benzo[1,3]oxathiol-5-ylmethyl)-succinamic acid tert-butyl ester 

Relevant academic research and scientific papers

Application of reversible amide-bond protection to suppress peptide segment epimerisation

Reversible alkylation of the C-terminal amide-bond of a protected peptide segment with 2-hydroxy-4-methoxybenzyl dramatically suppresses epimerisation during activation and coupling. However, due to the formation of a 4,5-dihydro-8-methoxy-1,4-benzoxazepin-2(3H)-one species upon activation the rate of coupling is low. A safety-catch amide-bond protecting group, 6-hydroxy-5-methyl-1,3- benzoxathiolyl, has been designed to suppress epimerisation and couple with excellent yield.