5234-75-3

Basic information

• Product Name: (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine
• Synonyms: (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine
• CAS NO: 5234-75-3
• Molecular Weight: 579.716
• Mol File: 5234-75-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine(5234-75-3)
• EPA Substance Registry System: (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine(5234-75-3)

Safety Data

• Hazardous Substances Data: 5234-75-3(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 118329-82-1 (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine 
• 51-35-4 4R-4-hydroxyproline 
• 116143-08-9 (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 57850-05-2 (2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine 

Downstream Products

• 125109-58-2 (1S,4S)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 59436-77-0 (1S,4S)-2-Methyl-2,5-diazabicyclo-[2.2.1]heptane 
• 100944-15-8 (1S,4S)-2-Benzyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 132666-68-3 (1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane 
• 113451-59-5 (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 
• 118354-72-6 (1R,4R)-2-(4-tolylsulfonyl)-5-(phenylmethyl)-2,5-diazabicyclo<2.2.1>heptane 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 1032278-49-1 (1S,4S)-5-hydroxypropyl-2-tosyl-2,5-diazabicyclo[2.2.1]heptane 
• 1032278-20-8 (1S,4S)-5-butyl-2-tosyl-2,5-diazabicyclo[2.2.1]heptane 

Relevant articles and documents

Multicomponent synthesis of some new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro anti-proliferative activity against CaSki, MDA-MB-231 and SK-Lu-1 tumour cells as apoptosis inducing agents without necrosis

Identification of a new class of antitumor agent capable to induce apoptosis without triggering necrotic cell death event is challenging. The present communication describes the multicomponent synthesis of seven new (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-dithiocarbamates and their in vitro antiproliferative activity on cervical cancer cell line (CaSki), breast cancer cell line (MDA-MB231), lung cancer cell line (SK-Lu-1) and human lymphocytes. Among the synthesized dithiocarbamates, compound 9e displayed significant antiproliferative activity without inducing any necrotic cell death (both on tumour cells and lymphocytes) and induced apoptosis in tumor cells by the caspase dependent apoptotic pathway. The compound 9e also exhibited greater tumor selectivity than human lymphocytes. In silico ADME predictions revealed that compound 9e has the potential to be developed as a drug candidate. Rapid chemical modifications of this lead are thus highly necessary for further investigation as a drug like safer antitumor candidate and also to achieve compounds with better activity profile.

Synthesis of novel derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane and their evaluation as potential ligands in asymmetric catalysis

Thirty-seven (most of them novel) chiral derivatives of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (2-36, 38, 39) were prepared from (S)-trans-4-hydroxyproline. A selection of these chiral ligands were examined as potential ligands in the preparation of catalysts for the enantioselective addition of diethylzinc to aldehydes and as chiral Lewis acid activators in the asymmetric Diels-Alder reaction. In the former system, diamine 30 induced up to 92 % enantiomeric excess in the formation of (S)-phenyl ethyl carbinol, whereas in the case of the cycloaddition reaction between cyclopentadiene and 3-acryloyloxazolidin-2-one the catalytic complex formed between dimeric derivative 8 and copper triflate [Cu(OTf)2] afforded the expected product in a 95:5 endo/exo ratio and up to 72 % ee for the major diastereomeric product. Finally, some of the novel chiral diamines prepared in this work were also evaluated as potential organocatalysts in the asymmetric amination of ethyl α-phenyl-α-cyano acetate. Bifunctional derivative 12 provided the animated product in excellent yield and with up to 40 % ee. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of (1R,4R)- and (1S,4S)-2,5-diazabicyclo[2.2.1]heptanes and their N-substituted derivatives

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