270901-32-1

Upstream product

• 1201096-17-4 C₃₉H₅₁ClN₂O₉ 
• 186256-68-8 cryptophycin 53 
• 270901-33-2 2-(3-tert-butoxycarbonylamino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid 4-[2-(3-chloro-4-methoxy-phenyl)-1-(2,2,2-trichloro-ethoxycarbonyl)-ethylcarbamoyl]-1-(2,3-dihydroxy-1-methyl-3-phenyl-propyl)-but-3-enyl ester 
• 326603-47-8 ethyl (3S)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate 
• 326603-41-2 ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate 
• 866343-53-5 (2R,3S)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butyl 4-methylbenzenesulfonate 
• 866343-51-3 tert-butyl (5S,6S,E)-5-(allyloxy)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-hept-2-enoate 
• 866343-41-1 (5S,6S,2E)-tert-butyl 6-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5-hydroxyhept-2-enoate 
• 866343-50-2 ethyl (2R,3R)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butanoate 
• 866343-47-7 ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate 
• 866343-54-6 (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanenitrile 
• 866343-43-3 (2R,3S)-2-(allyloxy)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-butan-1-ol 
• 866343-42-2 ethyl (2R,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate 
• 866343-44-4 (3S,4S)-3-(allyloxy)-4-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]pentanal 

Downstream Products

• 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] 
• 186256-67-7 cryptophycin 52 
• 270901-35-4 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-16-[(S)-1-((4R,5R)-2-methoxy-5-phenyl-[1,3]dioxolan-4-yl)-ethyl]-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 
• 270901-34-3 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-16-[(S)-1-((4R,5R)-2-methoxy-2-methyl-5-phenyl-[1,3]dioxolan-4-yl)-ethyl]-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 

Relevant academic research and scientific papers

Efficient synthesis of cryptophycin-52 and novel para- Alkoxymethyl unit A analogues

Cryptophycins are a family of highly cytotoxic, cyclic depsipeptides. They display antitumour activity that is largely maintained for multidrug-resistant tumour cells. Cryptophycins are composed of four building blocks (units A-D) that correspond to the respective amino and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres in a short, efficient and reliable synthesis and con-tributes to an easier and faster synthesis of cryptophycins. The first two stereogenic centres are introduced by a catalytic asymmetric dihydroxylation, whereas the remaining two stereogenic centres are introduced with substrate control of diastereoselectivity. The stereogenic diol function also serves as the epoxide precursor. The approach was used to synthesise the native unit A building block as well as three paraalkoxymethyl analogues from which cryptophycin-52 and three analogous cryptophycins were prepared. Macrocyclisation of the seco-depsipeptides was based on ring-closing metathesis.

Efficient and versatile stereoselective synthesis of cryptophycins

The cryptophycins are a family of cyclic depsipeptides with four retrosynthetic units A to D which correspond to the respective amino acids and hydroxy acids. A new synthetic route to unit A allows the selective generation of all four stereogenic centres

Cryptophycin compounds

The present invention provides cryptophycin compounds of Formula I that are useful in the treatment of neoplasms.

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.