1581267-11-9

Basic information

• Product Name: (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone
• Synonyms: (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone
• CAS NO: 1581267-11-9
• Molecular Weight: 1148.68
• Mol File: 1581267-11-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone(1581267-11-9)
• EPA Substance Registry System: (2S,6R,9S,12R,13S)-12-[(S)-isobutyl]-13-(tert-butyldimethylsilyloxy)-6-[2-(methylthio)ethyl]-2-[(E)-4-(tritylthio)but-1-en-1-yl]-9-tritylthiomethyl-1-oxa-5,8,11-triazacyclopentadecane-4,7,10,15-tetraone(1581267-11-9)

Safety Data

• Hazardous Substances Data: 1581267-11-9(Hazardous Substances Data)

Upstream product

• 21691-49-6 D-methionine methyl ester 
• 1581266-95-6 (R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enamide]-4-(methylthio)butanoic acid 
• 1027785-31-4 (S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoic acid 
• 1581266-93-4 methyl (R)-2-{(S,E)-3-[(4-methoxybenzyl)oxy]-7-(tritylthio)hept-4-enamido}-4-(methylthio)butanoate 

Relevant articles and documents

Total synthesis of burkholdacs A and B and 5,6,20-tri-epi-burkholdac A: HDAC inhibition and antiproliferative activity

The bicyclic depsipeptide histone deacetylase (HDAC) inhibitors burkholdacs A and B were efficiently synthesized in a highly convergent and unified manner. The synthesis features the amide coupling of a d-valine-d-cysteine- or d-allo-isoleucine-d-cysteine-containing segment with a d-methionine-containing segment to directly assemble the corresponding seco-acids, key precursors for macrolactonization. Using the same methodology, 5,6,20-tri-epi-burkholdac A was also synthesized. HDAC inhibitory assays and cell-growth inhibition analyses of the synthesized depsipeptides demonstrated the potency order of this class of bicyclic depsipeptides as compared to the clinically approved depsipeptide FK228 (romidepsin). Novel structure-activity relationships within this class of compounds were also revealed.