1585181-21-0

Basic information

• Product Name: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate
• Synonyms: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate
• CAS NO: 1585181-21-0
• Molecular Weight: 517.689
• Mol File: 1585181-21-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate(1585181-21-0)
• EPA Substance Registry System: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate(1585181-21-0)

Safety Data

• Hazardous Substances Data: 1585181-21-0(Hazardous Substances Data)

Upstream product

• 21947-98-8 N-tert-butyloxycarbonyl-S-trityl-L-cysteine 
• 158861-38-2 (R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide 
• 149910-63-4 N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1333536-66-5 C₂₇H₂₉NO₂S 
• 1333536-82-5 (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester 
• 1333536-68-7 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-5-(2,2,2-trichloroethoxycarbonyloxy)-3-methylhept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 
• 1334149-94-8 apratoxin S₄ 
• 1585181-22-1 ethyl (R)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanonate 
• 1094435-87-6 C₂₉H₃₃NO₄S 
• 1585181-32-3 pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3,6-dimethyl-5-(2,2,2-trichloroethoxycarbonyloxy)-hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 
• 1585186-80-6 apratoxin S₁₀ 

Relevant articles and documents

Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling

The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/Li

Total and semi-syntheses of antimicrobial thuggacin derivatives

The total and semi-synthesis of 13 new macrolactones derived from thuggacin, which is a secondary metabolite from the myxobacterium Sorangium cellulosum, are reported. The thuggacins have attracted much attention due to their strong antibacterial activity, particularly towards Mycobacterium tuberculosis. This study focuses on 1) thuggacin derivatives that cannot equilibrate by transacylation between the three natural thuggacins A-C, 2) the roles of the thiazole ring, and 3) the hexyl side chain at C2. Semi-synthetic O-methylation at C17 suppressed the transacylations without a substantial loss of antibacterial activity. Exchanging the C17-C25 side chain for simplified hydrophobic chains led to complete loss of antibacterial activity. Exchange of the thiazole by an oxazole ring or removal of the hexyl side chain at C2 had no substantial effect on the biological properties.