88043-21-4

Basic information

• Product Name: N-Boc-trans-4-tosyloxy-L-proline methyl ester
• Synonyms: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-Methylphenyl)sulfonyl]oxy]-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4R)-;(4R)-4-TsO-N-Boc-Pro-OMe;BOC-trans-4-tosyloxy-L-proline methyl ester:(4R)-4-TsO-N-Boc-Pro-OMe;N-(tert-Butoxycarbonyl)-trans-4-(p-toluenesulfonyloxy)-L-proline Methyl Ester;N-Boc-trans-4-(p-tosyloxy)-L-proline methyl ester ;N-BOC-TRANS-4-TOSYLOXY-L-PROLINE METHYL ESTER;N-TERT-BUTYLOXYCARBONYL-TRANS-4-P-TOLUYLSULFONYLOXY-L-PROLINE METHYL ESTER;N-TERT-BUTYLOXYCARBONYL-O-P-TOLUENESULFONYL-L-PROLINE METHYL ESTER
• CAS NO: 88043-21-4
• Molecular Formula: C₁₈H₂₅NO₇S
• Molecular Weight: 399.46
• Product Categories: Heterocyclic Compounds;Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 88043-21-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 77.0 to 81.0 °C
• Boiling Point: 520.5 °C at 760 mmHg
• Flash Point: 268.6 °C
• Appearance: /
• Density: 1.265 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• CAS DataBase Reference: N-Boc-trans-4-tosyloxy-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-trans-4-tosyloxy-L-proline methyl ester(88043-21-4)
• EPA Substance Registry System: N-Boc-trans-4-tosyloxy-L-proline methyl ester(88043-21-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 88043-21-4(Hazardous Substances Data)

Usage

Description

N-Boc-trans-4-tosyloxy-L-proline methyl ester is a colorless crystalline compound that serves as an important building block in organic synthesis, particularly in the preparation of complex organic molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
N-Boc-trans-4-tosyloxy-L-proline methyl ester is used as a key intermediate in the synthesis of bicycloazahydantoins, which are a class of compounds with potential applications as androgen receptor antagonists. These antagonists can be utilized in the development of drugs for the treatment of various androgen-dependent disorders, such as prostate cancer and benign prostatic hyperplasia.
Additionally, the compound's unique chemical properties, including its colorless crystalline nature, make it a valuable component in the synthesis of other complex organic molecules and pharmaceuticals, further expanding its applications in the pharmaceutical industry.

Upstream product

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 98-59-9 p-toluenesulfonyl chloride 
• 40350-82-1 1-(t-butoxycarbonyl)-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 144527-44-6 (2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride 
• 80-48-8 methyl p-toluene sulfonate 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 

Downstream Products

• 385440-93-7 (2S-trans)-2-hydroxymethyl-4-[[(4-methylphenyl)sulfonyl]oxy]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester 
• 385440-70-0 (2S,4R)-2-Formyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 385440-71-1 (2S-trans)-2-[cyano[(phenylmethyl)amino]methyl]-4-[[(4-methylphenyl)-sulfonyl]oxy]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester 
• 121148-01-4 (2S,4S)-4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 149152-68-1 (2S,4S)-1-tert-butyl 2-methyl 4-(((benzyloxy)carbonyl)amino)pyrrolidine-1,2-dicarboxylate 
• 185304-30-7 (2S,4S)-4-Benzyloxycarbonylamino-1-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid 
• 185304-45-4 (2S,4S)-4-Benzyloxycarbonylamino-1-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 185304-38-5 (2S,4S)-4-({(2S,4S)-4-Benzyloxycarbonylamino-1-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-pyrrolidine-2-carbonyl}-amino)-1-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid methyl ester 
• 149138-26-1 (2S,4S)-1-(t-butoxycarbonyl)-2-ethoxycarbonyl-4-benzoylthiopyrrolidine 
• 227935-38-8 (2S,4S)-4-(4-bromo-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 686766-49-4 (2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 1433280-45-5 (2S,4S)-4-morpholin-4-yl-pyrrolidine-1,2-dicarboxylic acid 2-[2-(4-bromo-phenyl)-2-oxo-ethyl]ester 1-tert-butyl ester 
• 1433280-46-6 (2S,4S)-2-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-morpholin-4-yl-pyrrolidine-1-carboxylic acid tert-butyl ester 

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The invention discloses a preparation method of trans-4-cyclohexyl-L-proline. The method comprises the following steps of (1) under the effect of an acid-binding agent, 4S-hydroxy-N-Boc-L-proline ester 6 and sulfonyl chloride are subjected to condensation to generate sulphonate 5, wherein R is C1-4 alkyl; (2) under the effects of a copper catalyst, lithium salt and organic alkali, the sulphonate 5and cyclohexylmagnesium bromide take nucleophilic substitution to generate a compound 4; (3) the compound 4 is hydrolyzed by lithium hydroxide to obtain (4S)-N-Boc-4-cyclohexyl-L-proline (a compound3); (4) the compound 3 is subjected to Boc removal under the condition of hydrochloric acid or trifluoroacetic acid/methylene dichloride; a target product 2 is prepared. The preparation method has thebeneficial effects that the target product structure and chirality are introduced through sulphonate and Grignard reagent nucleophilic substitution; the defects of the existing noble metal reductionmethod are overcome; the operation of the method is simple; the conditions are mild; the yield is good; the chemical purity and the optical purity are very high; the preparation method is suitable forindustrial production.