1581266-97-8

Basic information

• Product Name: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate
• Synonyms: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate
• CAS NO: 1581266-97-8
• Molecular Weight: 1312.88
• Mol File: 1581266-97-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate(1581266-97-8)
• EPA Substance Registry System: (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-(4-methoxybenzyloxy)-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate(1581266-97-8)

Safety Data

• Hazardous Substances Data: 1581266-97-8(Hazardous Substances Data)

Upstream product

• 21691-49-6 D-methionine methyl ester 
• 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 

Downstream Products

• 1581266-98-9 (3S,4R)-allyl 3-(tert-butyldimethylsiloxy)-4-{(S)-2-[(R)-2-[(S,E)-3-hydroxy-7-(tritylthio)hept-4-enoylamino]-4-(methylthio)butanoylamino]-3-tritylthio(propionylamino)}-5-methylhexanoate 

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.