119717-37-2

Basic information

• Product Name: jasplakinolide
• CAS NO: 119717-37-2
• Molecular Weight: 709.68
• Mol File: 119717-37-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: jasplakinolide(CAS DataBase Reference)
• NIST Chemistry Reference: jasplakinolide(119717-37-2)
• EPA Substance Registry System: jasplakinolide(119717-37-2)

Safety Data

• Hazardous Substances Data: 119717-37-2(Hazardous Substances Data)

Upstream product

• 943858-43-3 C₄₅H₆₅N₄O₆SiBr 
• 888494-83-5 (R)-3-(2-Bromo-1H-indol-3-yl)-2-methylamino-propionic acid methyl ester 
• 134876-93-0 (3S,4R,5S)-4-Iodo-3,5-dimethyl-dihydro-furan-2-one 
• 1149377-40-1 cyclo-[Ala-D-2-Br-N-MeTrp-βTyr(TIPS)-O-Htn] 
• 161925-50-4 (2S,4E,6S,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-en-1-al 
• 161925-45-7 methyl (R)-3-amino-3-<4-(tert-butyldimethylsiloxy)phenyl>propanoate 
• 161925-49-1 (2S,4E,6S,8S)-8-benzoyloxy-2,4,6-trimethylnon-4-en-1-ol 
• 161925-47-9 (2S,4E,6S,8S)-8-hydroxy-1-(methoxymethoxy)-2,4,6-trimethylnon-4-ene 
• 426207-35-4 (E)-methyl 3-(4-(tert-butyldimethylsilyloxy)phenyl)acrylate 
• 134781-89-8 methyl (2R,5S)-5-(tert-butoxycarbonylamino)-3-methyl-2-<(2-bromo-1H-indol-3-yl)methyl>-4-oxo-3-azahexanoate 
• 131791-79-2 (2,R,5S)-5-(tert-butoxycarbonylamino)-3-methyl-2-<(2-bromo-1H-indol-3-yl)methyl>-4-oxo-3-azahexanoic acid 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 161722-18-5 (2S,4E,6R,8S)-8-tert-butyldimethylsilyloxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester 
• 161722-15-2 (2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine 

Downstream Products

• 161925-59-3 jaspamide Z₁ 
• 103848-63-1 (E)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid [1-({2-(2-bromo-1H-indol-3-yl)-1-[3-hydroxy-1-(4-hydroxy-phenyl)-propylcarbamoyl]-ethyl}-methyl-carbamoyl)-ethyl]-amide 
• 102396-25-8 Acetic acid 4-[(E)-7-(2-bromo-1H-indol-3-ylmethyl)-8,10,13,15,17,19-hexamethyl-2,6,9,12-tetraoxo-1-oxa-5,8,11-triaza-cyclononadec-15-en-4-yl]-phenyl ester 

Relevant articles and documents

Synthesis and structure-activity correlation of natural-product inspired cyclodepsipeptides stabilizing F-actin

The fundamental role played by actin In the regulation of eukaryotic cell maintenance and motility renders it a primary target for small-molecule intervention. in this arena, a class of potent cytotoxic cyclodepsipeptide natural products has emerged over the last quarter-century to stimulate the fields of biology and chemistry with their unique actin-stabilizing properties and complex peptide-polyketide hybrid structures. Despite considerable research effort, a structural basis for the activity of these secondary metabolites remains elusive, not least for the lack of high-resolution structural data and a reliable synthetic route to diverse compound libraries. in response to this, an efficient solid-phase approach has been developed and successfully applied to the total synthesis of Jasplakinolide and chondramide C and diverse analogues. The key macrocylization step was realized using ruthenium-catalyzed ring-closing metathesis (RCM) that in the course of a library synthesis produced discernible trends in metathesis reactivity and E/Z-selectivity, After optimization, the RCM step could be operated under mild conditions, a result that promises to facilitate the synthesis of more extensive analogue libraries for structure-function studies. The growth inhibitory effects of the synthesized compounds were quantified and structure-activity correlations established which appear to be in good alignment with relevant biological data from natural products. in this way a number of potent unnatural and simplified analogues have been found. Furthermore, potentially important stereochemical and structural components of a common pharmacophore have been identified and rationalized using molecular modeling. These data will guide in-depth mode-of-action studies, especially into the relationship between the cytotoxicity of these compounds and their actin-perturbing properties, and should inform the future design of simplified and functionalized actln stabilizers as well.

Enantioselective total synthesis of (+)-jasplakinolide

An enantioselective total synthesis of (+)-jasplakinolide is described. The synthesis of the polyketide template utilized a diastereoselective syn-aldol, ortho-ester Claisen rearrangement followed by efficient conversion to a cyanide. The β-amino acid uni

Studies on the Novel Cyclodepsipeptides. A Total Synthesis of (+)-Jasplakinolide (Jaspamide)

Diastereocontrolled total synthesis of (+)-jasplakinolide (1) has been accomplished via coupling of the tetrapropionate-derived segment (9) with the tripeptide (10) followed by trichlorobenzoyl chloride-mediated macrolactonization.