162473-78-1

Basic information

• Product Name: desepoxyarenastatin A
• Synonyms: desepoxyarenastatin A
• CAS NO: 162473-78-1
• Molecular Weight: 590.717
• Mol File: 162473-78-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: desepoxyarenastatin A(CAS DataBase Reference)
• NIST Chemistry Reference: desepoxyarenastatin A(162473-78-1)
• EPA Substance Registry System: desepoxyarenastatin A(162473-78-1)

Safety Data

• Hazardous Substances Data: 162473-78-1(Hazardous Substances Data)

Upstream product

• 350245-17-9 (R)-(tert-butoxy)-(N-1-((4-methoxyphenyl)methyl)-2-oxo-2-(2-oxoazetidinyl)ethyl)formamide 
• 350245-13-5 (1S,3E)-4-N-((1R)-1-((4-methoxybenzyl)-2-oxo-2-(2-oxoazetidinyl)ethyl)carbamoyl)-1-((1R)-1-methyl-2-propenyl)but-3-enyl 4-methyl-2-[(tert-butyldimethylsilyl)oxy]pentanoate 
• 350245-08-8 (1S,3E)-4-N-((1R)-1-((4-methoxybenzyl)-2-oxo-2-(2-oxoazetidinyl)ethyl)carbamoyl)-1-((1R)-1-methyl-2-propenyl)but-3-enyl (2S)-2-hydroxy-4-methylpentanoate 
• 350245-11-3 (1S,2R)-1-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methylbut-3-enyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate 
• 350245-12-4 tert-butyl (2E)-(5S,6R)-5-[(2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoyloxy]-6-methylocta-2,7-dienoate 
• 350245-16-8 (5S,6R,2E)-6-methyl-5-((2S)-4-methyl-2-[(tert-butyldimethylsilyl)oxy]pentanoyloxy)octa-2,7-dienoic acid 
• 350245-15-7 (1S)-1-[(1R)-1-methylprop-2-enyl]-3-oxopropyl (2S)-4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)pentanoate 
• 350245-09-9 2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoyl chloride 
• 220249-55-8 (3S,4R)-1-(4-methoxybenzyloxy)-4-(trifluoromethyl)hex-5-en-3-ol 
• 68856-96-2 N-(tert-butoxycarbonyl)-O-methyl-D-tyrosine 
• 326473-59-0 (2S)-2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoic acid 
• 281190-97-4 (2R,3E,1'S,1''R,2''S)-1''-[(p-tolylsulfonyl)amino]indan-2''-yl 2-[3'-(benzyloxy)-1'-hydroxypropyl]-4-phenylbut-3-enoate 
• 281191-01-3 (2R,2'E,5'S,6'R,7'E)-tert-butyl 3-(4-methoxyphenyl)-2-({6'-methyl-8'-phenyl-5'-[(triisopropylsilanyl)oxy]octa-2',7'-dienoyl}amino)propionate 
• 281191-02-4 (2R,2'E,5'S,6'R,7'E)-tert-butyl 2-[(5'-hydroxy-6'-methyl-8'-phenylocta-2',7'-dienoyl)amino]-3-(4-methoxyphenyl)propionate 

Downstream Products

• 162600-54-6 C₃₃H₄₂O₇N₂CO 
• 162600-54-6 cryptophycin-24 
• 162600-54-6 cryptophycin-24 
• 162600-54-6 (E)-(3S,10R,16S)-3-Isobutyl-10-(4-methoxy-benzyl)-16-[(S)-1-((2S,3R)-3-phenyl-oxiranyl)-ethyl]-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 162600-54-6 arenastatin A 
• 162600-54-6 arenastatin A 

Relevant articles and documents

Frontiers and opportunities in chemoenzymatic synthesis

Natural product biosynthetic pathways have evolved enzymes with myriad activities that represent an expansive array of chemical transformations for constructing secondary metabolites. Recently, harnessing the biosynthetic potential of these enzymes through chemoenzymatic synthesis has provided a powerful tool that often rivals the most sophisticated methodologies in modern synthetic chemistry and provides new opportunities for accessing chemical diversity. Herein, we describe our research efforts with enzymes from a broad collection of biosynthetic systems, highlighting recent progress in this exciting field.

Asymmetric syntheses of potent antitumor macrolides cryptophycin B and arenastatin A

Efficient and highly stereoselective syntheses of cryptophycin B and arenastatin A, potent cytotoxic agents, are described. An ester-derived titanium enolate mediated syn-aldol reaction was employed to generate the stereocenters C-5 and C-6. The route is convergent and provides a convenient access to the synthesis of structural variants of cryptophycins as well as members of its family. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide

In order to produce stable analogs in blood of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized four analogs in which the 15-20 ester linkage was modified. Among them, the carba analog and 20-deoxo analog showed stability in serum. The conformation of arenastatin A and its three analogs were analyzed by distance-restrained molecular dynamic calculation to elucidate a three-dimensional stereostructure contributing to the extremely potent cytotoxicity of arenastatin A.