162600-54-6

Basic information

• Product Name: (2E)-N-[(1R,4E)-1-formyl-4-imino-1-(4-methoxybenzyl)-2-oxobutyl]-5-hydroxy-N-(2-hydroxy-4-methylpentanoyl)-6-(3-phenyloxiran-2-yl)hept-2-enamide
• CAS NO: 162600-54-6
• Molecular Formula: C₃₄H₄₂N₂O₈
• Molecular Weight: 606.7059
• Mol File: 162600-54-6.mol

Chemical Properties

• Boiling Point: 761.9°C at 760 mmHg
• Flash Point: 414.6°C
• Density: 1.21g/cm³
• Vapor Pressure: 2.11E-24mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: (2E)-N-[(1R,4E)-1-formyl-4-imino-1-(4-methoxybenzyl)-2-oxobutyl]-5-hydroxy-N-(2-hydroxy-4-methylpentanoyl)-6-(3-phenyloxiran-2-yl)hept-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-N-[(1R,4E)-1-formyl-4-imino-1-(4-methoxybenzyl)-2-oxobutyl]-5-hydroxy-N-(2-hydroxy-4-methylpentanoyl)-6-(3-phenyloxiran-2-yl)hept-2-enamide(162600-54-6)
• EPA Substance Registry System: (2E)-N-[(1R,4E)-1-formyl-4-imino-1-(4-methoxybenzyl)-2-oxobutyl]-5-hydroxy-N-(2-hydroxy-4-methylpentanoyl)-6-(3-phenyloxiran-2-yl)hept-2-enamide(162600-54-6)

Safety Data

• Hazardous Substances Data: 162600-54-6(Hazardous Substances Data)

Upstream product

• 162473-78-1 desepoxyarenastatin A 
• 733769-83-0 (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid (S)-1-[(S)-1-((2R,3R)-3-phenyl-oxiranyl)-ethyl]-but-3-enyl ester 
• 591-50-4 iodobenzene 
• 17355-19-0 methyl (R)-2-amino-3-(4-methoxyphenyl)propanoate 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 94790-24-6 (2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester 
• 733769-89-6 3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionic acid 
• 1026015-46-2 (S)-2-{3-[(R)-2-Acryloylamino-3-(4-methoxy-phenyl)-propionylamino]-propionyloxy}-4-methyl-pentanoic acid 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 2243-53-0 trans-styrylacetic acid 
• 37755-48-9 benzyl (2S)-2-hydroxy-4-methylpentanoate 
• 64205-12-5 N-α-benzyloxycarbonyl-D-tyrosine 
• 65806-89-5 (R)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propionic acid 
• 219606-82-3 (2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}propionyl)oxy]-4-methylpentanoate 

Relevant articles and documents

Total synthesis of cryptophycin-24 (arenastatin A) via Prins cyclization

A stereoselective synthesis of fragment A of cryptophycin is achieved utilizing the versatile Prins cyclization. Subsequently, the total synthesis of cryptophycin-24 (arenastatin A) has been accomplished by coupling it with the depsipeptide subunit.

Stereoselective total synthesis of arenastatin A, a spongean cytotoxic depsipeptide

A highly stereoselective total synthesis of arenastatin A, an extremely potent cytotoxic cyclic depsipeptide from marine sponge, was developed. The desired 7,8-β-epoxide in arenastatin A was constructed by asymmetric sulfur ylide-mediated epoxidation in g

Total synthesis and anti-tubulin activity of epi-C3 analogues of cryptophycin-24

Epi-C3-cryptophycin-24, epi-C3-m-chlorobenzyl-cryptophycin-24, and the corresponding styrenes were synthesized and tested in vitro against the MCF-7 and multidrug-resistant MCF-7/ADR breast cancer cell lines and in an in vitro tubulin assembly assay. The results demonstrate that the S configuration at the C3 stereocenter is not required to induce potent cytotoxicity and the m-Cl substituent present on the C10 side chain did not induce any large change in activity.

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).

RCM approach for the total synthesis of cryptophycin-24 (Arenastatin A)

An efficient total synthesis of cryptophycin-24 (arenastatin A) is reported, which features two novel synthetic strategies, the use of a RCM reaction to form the macrocycle, and the introduction of the styrene epoxide moiety prior to the macrocyclization

Synthesis of Cryptophycins via an N-Acyl-β-lactam Macrolactonization

An efficient and concise approach to the synthesis of the macrolide core of the cryptophycins has been developed. A novel macrolactonization utilizing a reactive acyl-β-lactam intermediate incorporates the β-amino acid moiety within the 16-membered macrol

Rapid entry into the cryptophycin core via an acyl-beta-lactam macrolactonization: total synthesis of cryptophycin-24.

[see structure]. An efficient, concise approach to the macrolide core of the cryptophycins, potent antimitotic agents, has been achieved. The reaction sequence features a novel macrolactonization utilizing a reactive acyl-beta-lactam intermediate that inc

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.

Total synthesis of cryptophycin-24 (arenastatin A) amenable to structural modifications in the C16 side chain

Two efficient protocols for the synthesis of tert-butyl (5S,6R,2E,7E)-5-[(tert-butyldimethylsilyl)-oxy]-6-methyl-8-phenyl-2,7-octadie noate, a major component of the cryptophycins, are reported. The first utilized the Noyori reduction and Frater alkylation of methyl 5-benzyloxy-3-oxopentanoate to set two stereogenic centers, which became the C16 hydroxyl and C1' methyl of the cryptophycins. The second approach started from 3-p-methoxybenzyloxypropanal and a crotyl borane reagent derived from (-)-α-pinene to set both stereocenters in a single step and provided the dephenyl analogue, tert-butyl (5S,6R,2E)-5-[(tert-butyldimethylsilyl)oxy]-6-methyl-2,7-octadienoate, in five steps. This compound was readily converted to the 8-phenyl compound via Heck coupling. The silanyloxy esters were efficiently deprotected and coupled to the C2-C10 amino acid fragment to provide desepoxyarenastatin A and its dephenyl analogue. The terminal olefin of the latter was further elaborated via Heck coupling. Epoxidation provided cryptophycin-24 (arenastatin A).

Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae

A convergent synthesis of cryptophycins has been developed in which (5S,6R)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic acid (A) is coupled with an amino acid segment (B). Two stereo-selective routes to A are described, the first employing allylatio