2584-71-6

Basic information

• Product Name: cis-4-Hydroxy-D-proline
• Synonyms: (2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID;(2R,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;(4R,2R)-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID;D-ALLO-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID;D-ALLO-HYDROXYPROLINE;D-CIS-4-HYDROXYPROLINE;D-CIS-HYDROXYPROLINE;CIS-4-HYDROXY-D-PROLINE
• CAS NO: 2584-71-6
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.13
• EINECS: 219-963-5
• Product Categories: Carboxylic Acids;Pyrrolidines;chiral;Chiral reagent;Chiral Compound;Carboxylic Acids;Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 2584-71-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 243 °C (dec.)(lit.)
• Boiling Point: 242.42°C (rough estimate)
• Flash Point: 168.6 °C
• Appearance: White/Powder
• Density: 1.3121 (rough estimate)
• Vapor Pressure: 1.8E-06mmHg at 25°C
• Refractive Index: 1.4300 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Water (Slightly)
• PKA: 2.14±0.40(Predicted)
• Water Solubility: 5 g/100 mL
• BRN: 81439
• CAS DataBase Reference: cis-4-Hydroxy-D-proline(CAS DataBase Reference)
• NIST Chemistry Reference: cis-4-Hydroxy-D-proline(2584-71-6)
• EPA Substance Registry System: cis-4-Hydroxy-D-proline(2584-71-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-22-36/37/39-27-26
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 2584-71-6(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

cis-4-Hydroxy-D-proline (cas# 2584-71-6) is a compound useful in organic synthesis.

Definition

ChEBI: D-proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (R-configuration).

Biochem/physiol Actions

Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.

InChI:InChI=1/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m0/s1

Upstream product

• 114676-47-0 (2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 135042-12-5 (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline 
• 171192-72-6 (2R,4R)-ethyl N¹-benzyl-4-hydroxypyrrolidine-2-carboxylate 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 176966-56-6 (2R,4R,1'S)-1-(1'-phenylethyl)-4-hydroxy-proline methyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 232262-82-7 (R)-4-oxo-1,2-pyrrolidinedicarboxylic acid dimethyl ester 
• 33996-33-7 oxaceprol 
• 502442-57-1 ethyl (4R)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-2-pentenoate 
• 502442-54-8 ethyl (4R)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoa 
• 77450-00-1 (2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 444313-67-1 (1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 
• 232262-93-0 (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid dimethyl ester 
• 46122-47-8 (2S,4R)-O-acetyl-4-hydroxyproline 

Downstream Products

• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 135042-12-5 (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline 
• 256487-77-1 (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 203934-42-3 methyl-1N-(4-methoxyphenylsulfonyl)-4-oxo-pyrrolidine-(2R)-carboxylate 
• 247058-82-8 methyl-1N-(4-methoxyphenylsulfonyl)-4-methylenepyrrolidine-(2R)-carboxylate 
• 203934-64-9 methyl 1N-(4-n-butoxyphenyl)sulfonyl-4-oxo-pyrrolidine-(2R)-carboxylate 
• 256488-00-3 methyl 1N-(4-n-butoxyphenyl)sulfonyl-4-(N-methoxyamino)pyrrolidine-(2R)-carboxylate 
• 247058-65-7 methyl 1N-(4-n-butoxyphenyl)sulfonyl-4-(Z,E-N-methoxyimino)pyrrolidine-(2R)-carboxylate 
• 247058-70-4 Methyl-1N-[4-(4-Fluorophenoxy)phenyl]sulfonyl-4R-hydroxy-pyrrolidine-2R-carboxylate 
• 323205-04-5 [(2R,4S)-4-(6-Benzyloxycarbonylamino-purin-9-yl)-2-(tert-butoxycarbonylamino-methyl)-pyrrolidin-1-yl]-acetic acid methyl ester 

Relevant articles and documents

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Chemoenzymatic Synthesis of cis-4-Hydroxy-D-proline

Candida antarctica lipase fraction B (CALB) catalyzed the hydrolysis of the (S)-enantiomer of racemic 4-oxo-1,2-pyrrolidinedicarboxylic acid dimethyl ester with high enantioselectivity (> 99.5% ee at 51% conversion). Regioselective hydrogenation of the isolated (R)-4-oxo-1,2-pyrrolidinedicarboxylic acid dimethyl ester produced (2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylic acid dimethyl ester in 98% yield, and subsequent hydrolysis of the ester and N-(alkoxycarbonyl) groups produced cis-4-hydroxy-D-proline in 98% yield and 96% de. Diastereomeric mixtures of 4-hydroxy-1,2-pyrrolidinedicarboxylic acid dimethyl esters were also resolved using CALB to produce cis-4-hydroxy-D-proline or trans-4-hydroxy-L-proline in 93 to > 99.5% diastereomeric excess.

INHIBITORS OF CYCLIN DEPENDNT KINASE 7 (CDK7)

The present invention provides novel compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases (e.g., cancers (e.g., leukemia, melanoma, multiple myeloma), benign neoplasms, angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases) in a subject. Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the aberrant activity of cyclin-dependent kinase 7 (CDK7), and therefore, induce cellular apoptosis and/or inhibit transcription in the subject.

A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines

A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2S,4S)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity.