114676-69-6

Basic information

• Product Name: METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE
• Synonyms: (2R,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylicacid 1-(1,1-dimethylethyl) 2-methyl ester;(2R,4R)-1-tert-butyl 2-Methyl 4-hydroxypyrrolidine-1,2-dicarboxy;(2R,4R)-1-tert-butyl 2-Methyl 4-hydro×ypyrrolidine-1,2-dicarbo×ylate;Boc-Cis-D-Hyp-OMe;Methyl cis-Boc-4-hydroxy-D-prolinate;Methy cis-1-Boc-4-hydroxy-D-prolinate;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, (2R,4R)-;1-tert-butyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS NO: 114676-69-6
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.27
• EINECS: 1592732-453-0
• Mol File: 114676-69-6.mol
• Article Data: 77

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 335.2 °C at 760 mmHg
• Flash Point: 156.6 °C
• Appearance: White/Powder
• Density: 1.216 g/cm³
• Vapor Pressure: 8.47E-06mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 14.27±0.40(Predicted)
• CAS DataBase Reference: METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE(114676-69-6)
• EPA Substance Registry System: METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE(114676-69-6)

Safety Data

• Hazardous Substances Data: 114676-69-6(Hazardous Substances Data)

Usage

General Description

Methyl cis-1-BOC-4-hydroxy-D-prolinate is a chemical compound used in organic synthesis and pharmaceutical research. It is a derivative of proline, a naturally occurring amino acid, and the BOC (tert-butyloxycarbonyl) group is a protective group commonly used in organic chemistry to temporarily block a specific functional group. METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE is known for its role as a versatile building block in the synthesis of various pharmaceuticals and biologically active molecules. Its structure and properties make it a valuable tool in the development of new drug candidates and potential therapeutic agents. Additionally, its use in peptide synthesis and as a chiral auxiliary further demonstrates its significance in the field of medicinal chemistry and drug discovery.

InChI:InChI=1/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8-/m1/s1

Upstream product

• 148017-37-2 (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine 
• 168264-25-3 Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 81102-38-7 cis-L-hydroxyproline methyl ester 
• 67-56-1 methanol 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 188109-82-2 (2S,4S)-1-tert-butyl 2-methyl 4-acetoxypyrrolidine-1,2-dicarboxylate 
• 121147-94-2 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 186581-53-3 diazomethane 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 250122-38-4 (2R,4R)-4-benzyloxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 121147-97-5 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate 
• 169032-99-9 (2S,4S)-4-Chloro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 433289-68-0 cis-1-(Boc)-4-(4-bromo-phenoxy)-L-proline methyl ester 
• 211298-60-1 (2S,4R)-4-(Biphenyl-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 259214-70-5 (2S,4R)-4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848475-23-0 (2S,4S)-4-(3-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 438452-29-0 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate 
• 361367-93-3 N-tert-butoxycarbonyl-trans-4-(p-nitrobenzoyloxy)-D-proline methyl ester 
• 256487-77-1 (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 146060-25-5 O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 
• 244786-53-6 N-Boc-L-trans-Pro(4-<4-<(E)-2-(4-cyanophenyl)-1-diazenyl>phenoxy>)-OMe 
• 198969-28-7 (2R,4S)-4-Benzoyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 168264-26-4 (2S,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 

Relevant articles and documents

Design, Synthesis, and Biochemical Evaluation of Alpha-Amanitin Derivatives Containing Analogs of the trans-Hydroxyproline Residue for Potential Use in Antibody-Drug Conjugates

Alpha-amanitin, an extremely toxic bicyclic octapeptide extracted from the death-cap mushroom, Amanita phalloides, is a highly selective allosteric inhibitor of RNA polymerase II. Following on growing interest in using this toxin as a payload in antibody-drug conjugates, herein we report the synthesis and biochemical evaluation of several new derivatives of this toxin to probe the role of the trans-hydroxyproline (Hyp), which is known to be critical for toxicity. This structure activity relationship (SAR) study represents the first of its kind to use various Hyp-analogs to alter the conformational and H-bonding properties of Hyp in amanitin.

Synthesis process of N-BOC-cis-4-hydroxyproline methyl ester

The invention discloses a synthesis process of N-BOC-cis-4-hydroxyproline methyl ester. The synthesis process comprises the following steps: (1) adding raw materials including dichloromethane, 4-hydroxy-L-proline and DMAP into a 2 L reaction flask, stirring, slowly dropwise adding BOC anhydride into the reaction liquid, after dropwise adding, sampling, carrying out TLC, completely reacting the rawmaterials, adding water into the reaction liquid after treatment, stirring at a temperature of 20-30 DEG C, separating the liquid, drying an organic phase by using anhydrous sodium sulfate, and concentrating under reduced pressure to obtain a white solid product; and (2) taking the obtained product, adding tetrahydrofuran and DCC into a 5 L reaction flask, stirring at 20-30 DEG C to react for 1 hour, dropwise adding methanol into the reaction solution, keeping the temperature after dropwise adding, sampling, carrying out TLC until the reaction is complete, filtering the reaction solution, collecting the filtrate, concentrating under reduced pressure until no liquid flows out to obtain a white solid crude product, heating, collecting the filtrate, collecting a filter cake, and drying the filter cake to obtain a white solid. According to the invention, the product is prepared with high quality and high yield.

Substituted Quinazoline and Pyridopyrimidine Derivatives Useful as Anticancer Agents

Compounds of the general formula: processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.