186256-66-6

Upstream product

• 591-50-4 iodobenzene 
• 219660-54-5 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-16-((R)-1-methyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 
• 219621-70-2 (3S,4R)-4-methylhex-5-ene-1,3-diol 
• 642087-13-6 3-(diethoxyphosphinyl)-N-(3-chloro-4-methoxyphenyl)-D-alanine tert-butyl ester 
• 642087-16-9 ethyl (3S,4R)-3-acetoxy-4-methyl-6-phenylhexan-(5E)-oate 
• 281190-95-2 (R)-tert-butyl 2-amino-3-(4-methoxyphenyl)propionate 
• 180181-02-6 3-(tert-Butoxycarbonyl)amino-2,2-dimethylpropanoic Acid 
• 186193-10-2 (2S)-<3-<<(1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoic acid 
• 37755-48-9 benzyl (2S)-2-hydroxy-4-methylpentanoate 
• 186193-12-4 (S)-2-(3-Amino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(3-chloro-4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester 
• 642087-18-1 (2S)-2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid (1S,2R,2E)-1-{3-[1-tert-butoxycarbonyl-(2R)-2-(3-chloro-4-methoxyphenyl)ethylcarbamoyl]allyl}-2-methyl-4-phenyl-but-(3E)-enyl ester 
• 642087-17-0 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester 
• 642087-19-2 2-[2-(diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionic acid tert-butyl ester 

Downstream Products

• 204990-60-3 cryptophycin 52 
• 186256-67-7 cryptophycin 52 
• 186256-68-8 cryptophycin 53 
• 204397-62-6 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-5-hydroxy-6-methyl-7-oxo-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204398-55-0 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204397-44-4 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-16-[(E)-(R)-3-(4-methoxy-phenyl)-1-methyl-allyl]-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 204397-85-3 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 214463-38-4 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 204397-94-4 pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-(4-hydroxyphenyl)-6-methyl-1-oxo-2,7-octadienyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl, (3->1⁵)-lactone, (2S)- 
• 204397-86-4 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-5-hydroxy-6-[(2R,3R)-3-(3-methylphenyl)oxiranyl]-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl] 
• 561308-39-2 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-(2,5-dimethylphenyl)-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204397-88-6 cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-(3,4-dimethylphenyl)-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] 
• 204398-02-7 pentanoic acid, N-[(2E,5S,6R,7E)-8-[4-(aminomethyl)phenyl]-5-hydroxy-6-methyl-1-oxo-2,7-octadienyl]-3-chloro-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1)-lactone, (2S)- 
• 204398-12-9 4-(3-{(S)-1-[(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-ethyl}-oxiranyl)-benzoic acid methyl ester 

Relevant academic research and scientific papers

Intramolecular aminolysis of trichloroethyl esters: A mild macrocyclization protocol for the preparation of cryptophycin derivatives

The bifunctional catalyst 2-hydroxypyridine (2-pyridone) is shown to promote the intramolecular aminolysis of the polyfunctionalized long-chain amino trichloroethyl ester 8 to afford cryptophycin-51 (4). This process for the construction of the macrocycli

Enantioselective Synthesis of (+)-Cryptophycin 52 (LY355703), a Potent Antimitotic Antitumor Agent

A highly enantioselective and convergent synthesis of cryptophycin 52 (2), an exceedingly potent cytotoxic agent, is described. Cryptophycin 52, a synthetic variant of the cryptophycin family, is currently undergoing clinical trials. The synthesis is conv

Synthesis of Cryptophycin 52 Using the Sharpless Asymmetric Dihydroxylation: Diol to Epoxide Transformation Optimized for a Base-Sensitive Substrate

A synthesis of cryptophycin 52 (2) is reported using a Sharpless asymmetric dihydroxylation (AD) strategy to install the epoxide moiety. The high stereoselectivity of the AD reaction that allows for an efficient means of preparing the epoxide is in contrast to the standard direct epoxidation of cryptophycin substrates, which proceeds with poor diastereoselectivity. Methodology for conversion of the diol AD product to the requisite epoxide is disclosed. The transformation has been optimized to proceed in high yield in the presence of base sensitive functionality.

A novel approach for total synthesis of cryptophycins via asymmetric crotylboration protocol

Acyclic and a highly efficient stereoselective C-C bond formation of aldehyde 3 with the crotylboron reagent 4, derived from (-)-α-pinene, provided a homoallylic alcohol 6 in ≥99% enantio-(ee) and diastereomeric excess (de). The alcohol 6 was linearly con