173259-15-9

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 173259-14-8 ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-3,4-dihydroxybutyl>thiazole-4-carboxylate 
• 70-23-5 ethyl Bromopyruvate 
• 114684-69-4 methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate 
• 132970-32-2 methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate 
• 173259-11-5 (2S,4S)-2-benzyloxycarbonylamino-4,5-(isopropylidenedioxy)pentanamide 
• 173259-12-6 (2S,4S)-2-benzyloxycarbonylamino-4,5-(isopropylidenedioxy)pentanethioamide 
• 173259-13-7 ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-3,4-(isopropylidenedioxy)butyl>thiazole-4-carboxylate 

Downstream Products

• 173259-17-1 ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-hydroxy-3-(methoxymethoxy)butyl>thiazole-4-carboxylate 
• 173259-16-0 ethyl 2-<(1S,3S)-1-benzyloxycarbonylamino-4-t-butyldimethylsiloxy-3-(methoxymethoxy)butyl>thiazole-4-carboxylate 

Relevant academic research and scientific papers

Syntheses of 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic acid and the tripeptide skeleton of nosiheptide containing the acid

The stereoselective synthesis of an amino acid component called Fragment D, N,O-diprotected 2-[(1S,3S)-1-amino-3-carboxy-3-hydroxypropyl]thiazole-4-carboxylic acid of a macrobicyclic peptide antibiotic nosiheptide, was achieved by two routes. The dipeptide, Fragment B-C, 2-[(Z)-1-(N,O-isopropylidene-L-threonylamino)-1-propenyl]thiazole-4-ca rboxylic acid was also synthesized by the thiazole ring formation from (Z)-2-(N,O-diprotected L-threonylamino)-2-butenethioamide with ethyl bromopyruvate. The coupling of two components by using a condensing agent gave the expected tripeptide 2, which is an important partial skeleton of the nosiheptide.