102195-79-9

Basic information

• Product Name: N-Boc-cis-4-Hydroxy-L-proline methyl ester
• Synonyms: BOC-CIS-HYDROXYPROLINE-OME;BOC-CIS-HYP-OME;BOC-CIS-L-4-HYDROXYPROLINE METHYL ESTER;N-T-BOC-CIS-4-HYDROXY-L-PROLINE METHYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-CIS-4-HYDROXY-L-PROLINE METHYL ESTER;N-Boc-cis-4-hydroxy-L-proline Methyl ester, 97%, 97%;Boc-L-cis-4-Hydroxyproline methyl ester;1-tert-butyl 2-methyl cis-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS NO: 102195-79-9
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.27
• EINECS: 1592732-453-0
• Product Categories: Peptide Synthesis;Proline Derivatives;Unnatural Amino Acid Derivatives;Heterocycles
• Mol File: 102195-79-9.mol
• Article Data: 47

Chemical Properties

• Melting Point: 82-86 °C(lit.)
• Boiling Point: 335.244 °C at 760 mmHg
• Flash Point: 156.55 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: -15°C
• PKA: 14.27±0.40(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: N-Boc-cis-4-Hydroxy-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cis-4-Hydroxy-L-proline methyl ester(102195-79-9)
• EPA Substance Registry System: N-Boc-cis-4-Hydroxy-L-proline methyl ester(102195-79-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 102195-79-9(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 102195-79-9 differently. You can refer to the following data:
1. Used as a local anaesthetic. Used as therapeutic agents. Employed as important intermediates in various areas such as peptide synthesis, polymer chemistry..
2. 2S,4S)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester oline scaffold.

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-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 81102-38-7 cis-L-hydroxyproline methyl ester 
• 168264-25-3 Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester 
• 148017-37-2 (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine 
• 84520-68-3 N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester 
• 441067-49-8 (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 

Downstream Products

• 121147-97-5 1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate 
• 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 
• 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 
• 433289-65-7 (2S,4S)-4-(4-Cyano-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 
• 877068-90-1 (2S,4R)-4-[2-(2-Isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 791-28-6 Triphenylphosphine oxide 
• 211297-02-8 N-{(2S,4R)-4-(2-Bromo-6-isobutyl-phenoxy)-1-[2-(2,4-difluoro-benzoyl)-benzoyl]-pyrrolidin-2-ylmethyl}-4-[2,4-dioxo-thiazolidin-(5Z)-ylidenemethyl]-benzamide 
• 211296-91-2 N-{(2S,4R)-4-(2-Bromo-6-isobutyl-phenoxy)-1-[2-(4-fluoro-benzoyl)-benzoyl]-pyrrolidin-2-ylmethyl}-4-[2,4-dioxo-thiazolidin-(5Z)-ylidenemethyl]-benzamide 
• 630422-31-0 C₂₆H₂₉N₃O₆ 

Relevant articles and documents

Diastereoselectivity in the alkylation of 4-fluoroproline methyl esters

The reaction of alkylation of cis- and trans-4-fluoro-N-Boc-l-proline methyl esters has been examined by exposing their lithium enolates to a range of alkylating agents. The process showed a high degree of facial diastereoselectivity (except when methyl iodide was used as alkylating agent), invariably giving rise to products bearing the alkyl group in anti with respect to the fluorine atom. A tentative model to account for the observed stereoselectivity is also proposed.

Total Synthesis and Stereochemical Revision of the 2-Formylpyrrole Alkaloid Hemerocallisamine i

The first total synthesis of the 2-formylpyrrole alkaloid hemerocallisamine I is reported. The convergent synthesis features a key Maillard-Type condensation of a complex amine derived from cis-4-hydroxy-l-proline with a dihydropyranone, to directly furnish the 2-formylpyrrole ring system. The absolute configuration of hemerocallisamine I has been revised on the basis of optical rotation data obtained for the synthesized compound.

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.

Cross-Linked Collagen Triple Helices by Oxime Ligation

Covalent cross-links are crucial for the folding and stability of triple-helical collagen, the most abundant protein in nature. Cross-linking is also an attractive strategy for the development of synthetic collagen-based biocompatible materials. Nature uses interchain disulfide bridges to stabilize collagen trimers. However, their implementation into synthetic collagen is difficult and requires the replacement of the canonical amino acids (4R)-hydroxyproline and proline by cysteine or homocysteine, which reduces the preorganization and thereby stability of collagen triple helices. We therefore explored alternative covalent cross-links that allow for connecting triple-helical collagen via proline residues. Here, we present collagen model peptides that are cross-linked by oxime bonds between 4-aminooxyproline (Aop) and 4-oxoacetamidoproline placed in coplanar Xaa and Yaa positions of neighboring strands. The covalently connected strands folded into hyperstable collagen triple helices (Tm 80 °C). The design of the cross-links was guided by an analysis of the conformational properties of Aop, studies on the stability and functionalization of Aop-containing collagen triple helices, and molecular dynamics simulations. The studies also show that the aminooxy group exerts a stereoelectronic effect comparable to fluorine and introduce oxime ligation as a tool for the functionalization of synthetic collagen.

(2 S,4 R)- and (2 S,4 S)-Perfluoro- tert -butyl 4-hydroxyproline: Two conformationally distinct proline amino acids for sensitive application in 19F NMR

(2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline were synthesized (as Fmoc-, Boc-, and free amino acids) in 2-5 steps. The key step of each synthesis was a Mitsunobu reaction with perfluoro-tert-butanol, which incorporated a perfluoro-tert-butyl group, with nine chemically equivalent fluorines. Both amino acids were incorporated in model α-helical and polyproline helix peptides. Each amino acid exhibited distinct conformational preferences, with (2S,4R)-perfluoro-tert-butyl 4-hydroxyproline promoting polyproline helix. Peptides containing these amino acids were sensitively detected by 19F NMR, suggesting their use in probes and medicinal chemistry.

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.