181141-24-2

Basic information

• Product Name: (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate
• Synonyms: (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate
• CAS NO: 181141-24-2
• Molecular Weight: 1059.4
• Mol File: 181141-24-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate(CAS DataBase Reference)
• NIST Chemistry Reference: (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate(181141-24-2)
• EPA Substance Registry System: (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate(181141-24-2)

Safety Data

• Hazardous Substances Data: 181141-24-2(Hazardous Substances Data)

Upstream product

• 1202021-32-6 (5E,7R,11R,14S,17E,20S)-methyl 17-ethylidene-11,20-diisopropyl-7-(4-methoxybenzyloxy)-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate 
• 180973-42-6 N-[(9-fluorenylmethoxy)carbonyl]-L-threonyl-L-valine methyl ester 
• 180973-36-8 (E)-5-Tritylsulfanyl-pent-2-enoic acid methyl ester 
• 180973-37-9 (E)-5-(tritylthio)-2-penten-1-ol 
• 180973-22-2 (2E)-5-[(triphenylmethyl)thio]-2-pentenal 
• 2409-87-2 methyl (2E)-penta-2,4-dienoate 
• 180973-41-5 (E)-(R)-3-Hydroxy-7-tritylsulfanyl-hept-4-enoic acid benzyl ester 
• 180973-31-3 (S)-2-[(2S,3R)-2-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-3-tritylsulfanyl-propionylamino}-3-(toluene-4-sulfonyloxy)-butyrylamino]-3-methyl-butyric acid methyl ester 
• 180973-30-2 (S)-2-((2S,3R)-2-{(S)-2-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-3-tritylsulfanyl-propionylamino}-3-hydroxy-butyrylamino)-3-methyl-butyric acid methyl ester 
• 180973-28-8 (S)-2-{(2S,3R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionylamino]-3-hydroxy-butyrylamino}-3-methyl-butyric acid methyl ester 
• 180973-32-4 (S)-2-{(Z)-2-[(S)-2-((R)-2-Amino-3-methyl-butyrylamino)-3-tritylsulfanyl-propionylamino]-but-2-enoylamino}-3-methyl-butyric acid methyl ester 
• 180973-26-6 (R,E)-3-hydroxy-7-(tritylthio)hept-4-enoic acid 
• 3695-77-0 triphenylmethanethiol 
• 4070-48-8 L-Valine methyl ester 

Downstream Products

• 181141-25-3 (5E,7R,11R,14S,17E,20S)-17-ethylidene-7-hydroxy-11,20-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-14-(tritylthiomethyl)-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid 
• 128517-07-7 romidepsin 
• 180973-35-7 (3S,9S,12R,16S)-6-eth-(Z)-ylidene-3,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-9-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraazacyclohexadecane-2,5,8,11,14-pentaone 

Relevant articles and documents

Total synthesis of the bicyclic depsipeptide hdac inhibitors spiruchostatins a and b, 5″-epi-spiruchostatin b, fk228 (fr901228) and preliminary evaluation of their biological activity

The bicyclic depsipeptide histone deacetylase (HDAC) inhibitors spiruchostatins A and B, 5″-ep(-spiruchostatin B and FK228 were efficiently synthesized in a convergent and unified manner. The synthetic method involved the following crucial steps : i) a JuliaKocienski olefination of a 1,3-propanediol-derived sulfone and a L- or Dmalic acid-derived aldehyde to access the most synthetically challenging unit, (35 or 3R,4E)-3-hydroxy-7- mercaptohept-4-enoic acid, present in a D-alanine- or D-valine-containing segment; ii) a condensation of a D-valine-D-cysteine- or D-allo-isoleucine-D- cysteinecontaining segment with a D-alanineor D-valine-containing segment to directly assemble the corresponding secoacids; and iii) a macrocyclization of a seco-acid using the Shiina method or the Mitsunobu method to construct the requisite 15- or 16-membered macrolactone. The present synthesis has established the C5″ stereochemistry of spiruchostatin B. In addition, HDAC inhibitory assay and the cell-growth inhibition analysis of the synthesized depsipeptides determined the order of their potency and revealed some novel aspects of structure-activity relationships. It was also found that unnatural 5″-epi-spiruchostatin B shows extremely high selectivity (ca. 1600-fold) for class I HDAC1 (IC50 = 2.4 nM) over class II HDAC6 (IC 50 = 3900nM) with potent cell-growth-inhibitory activity at nanomolar levels of IC50 values.

Total synthesis of the antitumor depsipeptide FR-901,228

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