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

• 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 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 77-78-1 dimethyl sulfate 
• 441067-49-8 (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 186581-53-3 diazomethane 
• 135042-12-5 (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline 
• 114676-47-0 (2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester 
• 256487-77-1 (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 534-17-8 caesium carbonate 

Downstream Products

• 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 
• 244786-53-6 N-Boc-L-trans-Pro(4-<4-<(E)-2-(4-cyanophenyl)-1-diazenyl>phenoxy>)-OMe 
• 146060-25-5 O2-methyl O1-tert-butyl (2S,4S)-4-(p-tolylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 
• 121147-97-5 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate 
• 361367-93-3 N-tert-butoxycarbonyl-trans-4-(p-nitrobenzoyloxy)-D-proline methyl ester 
• 438452-29-0 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromo-phenyl)sulfonyl]oxy}-pyrrolidine-1,2-dicarboxylate 
• 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 
• 848475-23-0 (2S,4S)-4-(3-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848475-29-6 (2R,4R)-4-(4-Chloro-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848475-21-8 (2S,4S)-4-(4-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 848475-22-9 (2R,4R)-4-(4-Bromo-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 686766-46-1 (2S,4S)-4-(4-chloro-benzyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 1361054-84-3 1-tert-butyl 2-methyl (2S,4S)-4-(4-nitrobenzenesulfonyloxy)pyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

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.

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.