120205-53-0

Basic information

• Product Name: L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl-
• Synonyms: L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl-;(3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate
• CAS NO: 120205-53-0
• Molecular Formula: C₂₆H₅₁N₃O₅
• Molecular Weight: 485.70024
• Mol File: 120205-53-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 593.9±50.0 °C(Predicted)
• Appearance: /
• Density: 0.995±0.06 g/cm3(Predicted)
• PKA: 13.95±0.46(Predicted)
• CAS DataBase Reference: L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl-(120205-53-0)
• EPA Substance Registry System: L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl-(120205-53-0)

Safety Data

• Hazardous Substances Data: 120205-53-0(Hazardous Substances Data)

Usage

General Description

L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl- is a chemical compound that is a derivative of valine, an essential amino acid. It contains a methyl group, a diMethylethoxy group, and a methoxy group, as well as a ketone and an amide functional group. L-ValinaMide, N,N-diMethyl-L-valyl-N-[(1S,2R)-4-(1,1-diMethylethoxy)-2-Methoxy-1-[(1S)-1-Methylpropyl]-4-oxobutyl]-N-Methyl- may have potential applications in the fields of pharmaceuticals, biochemistry, and molecular biology due to its structural and functional properties. Its specific uses and effects would depend on its interactions with other molecules and biological systems.

Upstream product

• 97800-78-7 N,N-Dimethyl-L-valine pentafluorophenyl ester 
• 120205-52-9 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 474645-22-2 tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate 
• 154633-73-5 tert-Butyl (3S,4S,5S)-3-methoxy-4--5-methylheptanoate 
• 120205-56-3 benzyl methyl[(2S,3S)-3-methyl-1-oxopentan-2-yl]carbamate 
• 120205-55-2 benzyl [(2S,3S)-1-hydroxy-3-methylpentan-2-yl]methylcarbamate 
• 120205-57-4 tert-Butyl (3S,4S,5S)-3-hydroxy-4--5-methylheptanoate 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 540-88-5 acetic acid tert-butyl ester 
• 149664-79-9 (3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester 
• 120205-58-5 tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate 
• 135383-56-1 (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid 
• 120205-48-3 tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 

Downstream Products

• 110417-88-4 dolastatin 10 

Relevant articles and documents

Process Development and GMP Production of a Conjugate Warhead: Auristatin F-HPA-Ala/TFA (XMT-1864/TFA)

An efficient, large-scale manufacturing process is described for XMT-1864/TFA (1-TFA), an auristatin F derivative, used as a novel, highly potent, cytotoxic warhead in Mersana's oncology antibody-drug conjugate platforms. The process achieves high diastereomeric purity and controls the impurities with all intermediates readily isolated by crystallization or precipitation in high yield and purity. Protecting groups were selected to ensure tolerability, scalability, and stability of the intermediates under various solution-phase peptide coupling conditions. Crystallization of the final product was developed to remove specified impurities and provide a high-purity active warhead molecule for use in the bioconjugation processing. The convergent synthesis involving six non-GMP steps and five GMP steps has been carried out in multiple cGMP productions on 1-kg scale to produce 1-TFA in >98% chemical purity and 1% total diastereomeric contamination with ～50% overall yield for the GMP steps.

Synthesis and evaluation of novel dolastatin 10 derivatives for versatile conjugations

Dolastatin 10 (1) is a highly potent cytotoxic microtubule inhibitor (cytotoxicity IC50 5.0 nM) and several of its analogs have recently been used as payloads in antibody drug conjugates. Herein, we describe the design and synthesis of a series of novel dolastatin 10 analogs useful as payloads for conjugated drugs. We explored analogs containing functional groups at the thiazole moiety at the C-terminal of dolastatin 10. The functional groups included amines, alcohols, and thiols, which are representative structures used in known conjugated drugs. These novel analogs showed excellent potency in a tumor cell proliferation assay, and thus this series of dolastatin 10 analogs is suitable as versatile payloads in conjugated drugs. Insights into the structure–activity relationships of the analogs are also discussed.

Dolastatins 24. Synthesis of (-)-dolastatin 10. X-Ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleuine tert-butyl ester

Total synthesis of the extraordinary antineoplastic constituent, dolastatin 10, from the Indian Ocean mollusc Dolabella auricularia has been summarized. The final synthetic step involved diethyl cyanophosphonate-mediated coupling of Dov-Val-Dil with Dap-Doe. Improved syntheses of these important precursors has led to a very practical synthesis of natural dolastatin 10. Important details of the HPLC and high-field (500 MHz) NMR characterization techniques employed to confirm the purity of dolastatin 10 have been recorded. Copyright 1996 by the Royal Society of Chemistry.