3850-40-6

Basic information

• Product Name: Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)
• Synonyms: Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI);Boc-DL-serine;Serine,N-[(1,1-diMethylethoxy)carbonyl]-;(Tert-Butoxy)Carbonyl DL-Ser-OH
• CAS NO: 3850-40-6
• Molecular Formula: C₈H₁₅NO₅
• Molecular Weight: 205.2084
• Product Categories: N-BOC
• Mol File: 3850-40-6.mol

Chemical Properties

• Boiling Point: 385.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.240±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)(3850-40-6)
• EPA Substance Registry System: Serine, N-[(1,1-dimethylethoxy)carbonyl]- (9CI)(3850-40-6)

Safety Data

• Hazardous Substances Data: 3850-40-6(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Pharmaceutical Industries:
Serine, N-[(1,1-dimethylethoxy)carbonyl](9CI) is used as a building block for the synthesis of peptide-based drugs and biologically active compounds. Its protective group plays a vital role in the synthesis process by shielding the nitrogen atom from unwanted reactions, thereby enhancing the efficiency and selectivity of peptide synthesis.
Used in Peptide Synthesis:
In the field of peptide synthesis, Serine, N-[(1,1-dimethylethoxy)carbonyl](9CI) is employed as a protected amino acid. The N-[(1,1-dimethylethoxy)carbonyl] group ensures that the serine derivative can be selectively incorporated into growing peptide chains without participating in side reactions that could compromise the integrity and yield of the final product.
Used in Drug Development:
Serine, N-[(1,1-dimethylethoxy)carbonyl](9CI) is utilized in drug development as a key component in the creation of novel peptide-based therapeutics. Its protective group allows for the precise assembly of complex peptide structures, which can be further modified or conjugated to other molecules to enhance their pharmacological properties, such as stability, bioavailability, and target specificity.

Upstream product

• 312-84-5 D-Serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 155846-56-3 (2R)-2-amino-3-hydroxypropanoic acid hydrochloride 
• 4530-20-5 BOC-glycine 
• 50-00-0 formaldehyd 
• 302-84-1 serin 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 113525-84-1 2-Oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 

Downstream Products

• 42116-50-7 2,4-Dinitrophenylester von BOC-D-Serin 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 92261-75-1 Boc-D-Ser-D-Ala-OBzl 
• 150807-11-7 (S)-2-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-hex-5-enoic acid benzyl ester 
• 98541-64-1 N-(tert-butyloxycarbonyl)-D-serine β-lactone 
• 165058-72-0 (S)-1-((R)-2-tert-Butoxycarbonylamino-3-hydroxy-propionyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 47173-80-8 N-Boc-D-serine(Bzl)-OH 
• 190586-78-8 N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190586-80-2 N-tert-butoxycarbonyl-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester 
• 330814-64-7 [2-hydroxy-1-(4-hydroxy-3-hydroxymethyl-phenylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 616881-82-4 (R)-2-tert-Butoxycarbonylamino-3-(3,4-difluoro-benzyloxy)-propionic acid 
• 501701-41-3 [-(2,4-dimethoxybenzyloxycarbamoyl)-2-hydroxy-ethyl]carbamic acid tert-butyl ester 
• 86123-95-7 (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid 
• 872413-85-9 N-tert-butoxycarbonylamino-O-thien-2-ylmethyl-D-serine 

Relevant articles and documents

?-LACTAMASE INHIBITOR AND USE THEREOF

Provided are a β-lactamase inhibitor of formula (I), or an ester, a stereoisomer or a pharmaceutically acceptable salt thereof, and a method of preparing the same. Further provided is a pharmaceutical composition comprising the β-lactamase inhibitor of formula (I), or the ester, the stereoisomer or pharmaceutically acceptable salt thereof. In addition, the present invention relates to a method for treating diseases caused by bacterial infection, which comprises administering the β-lactamase inhibitor of formula (I), or the ester, the stereoisomer or the pharmaceutically acceptable salt thereof to a patient or a subject in need.

High-efficiency preparation method of D-dencichine

The invention relates to a high-efficiency synthesis method of a hemostasis compound D-dencichine, comprising the following steps: firstly enabling D-serine to react with di-tert-butyl dicarbonate ester to generate Boc-D-serine, then generating Gabriel reaction with hydroxy of methylsulfonyl chloride activated Boc-D--serine to obtain N-alpha-Boc-D-alpha, beta-diaminopro, finally condensing with oxalate mono-methyl ester sylvite then performing hydrolytic acidification to obtain a dencichine crude product, and purifying to obtain a dencichine competitive product, with the product content reaching more than 99.8%. Compared with existing D-dencichine synthesis methods, the reaction condition is more mild, the operation is simple and convenient, the material cost is relatively low, and the hemostasis compound D-dencichine is environment-friendly, is suitable for industrial production, and solves the problem of resource for later development of clinical trial of D-dencichine.

Synthesis and bioactivities study of new antibacterial peptide mimics: The dialkyl cationic amphiphiles

The emergence of infectious diseases caused by pathogenic bacteria is widespread. Therefore, it is urgently required to enhance the development of novel antimicrobial agents with high antibacterial activity and low cytotoxicity. A series of novel dialkyl cationic amphiphiles bearing two identical length lipophilic alkyl chains and one non-peptidic amide bond were synthesized and tested for antimicrobial activities against both Gram-positive and Gram-negative bacteria. Particular compounds synthesized showed excellent antibacterial activity toward drug-sensitive bacteria such as S. aureus, E. faecalis, E. coli and S. enterica, and clinical isolates of drug-resistant species such as methicillin-resistant S. aureus (MRSA), KPC-producing and NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE). For example, the MIC values of the best compound 4g ranged from 0.5 to 2 μg/mL against all these strains. Moreover, these small molecules acted rapidly as bactericidal agents, and functioned primarily by permeabilization and depolarization of bacterial membranes. Importantly, these compounds were difficult to induce bacterial resistance and can potentially combat drug-resistant bacteria. Thus, these compounds can be developed into a new class of antibacterial peptide mimics against Gram-positive and Gram-negative bacteria, including drug-resistant bacterial strains.

AN IMPROVED PROCESS FOR THE PREPARATION OF LACOSAMIDE

The present invention relates to an improved process for the synthesis of (R)- Lacosamide in which free base of O-methyl-N-benzyl-D-Serinamide is not isolated before acylation. The process avoids the use of column chromatography and chiral resolution for the preparation of different stages of Lacosamide.

Total Synthesis of Plusbacin A3 and Its Dideoxy Derivative Using a Solvent-Dependent Diastereodivergent Joullié-Ugi Three-Component Reaction

Full details of our synthetic studies toward plusbacin A3 (1), which is a depsipeptide with antibacterial activity, and its dideoxy derivative are described. To establish an efficient synthetic route of 1, a solvent-dependent diastereodivergent Joullié-Ugi three-component reaction (JU-3CR) was used to construct trans-Pro(3-OH) in a small number of steps. Two strategies were investigated toward the total synthesis. In the first synthetic strategy, the key steps were the trans-selective JU-3CR and a macrolactonization at the final stage of the synthesis. The JU-3CR using alkyl isocyanides in 1,1,1,3,3,3-hexafluoroisopropanol provided the trans products, and the coupling of the fragments to prepare the macrocyclization precursor proceeded smoothly. However, attempts toward the macrolactonization did not provide the desired product. Then, the second strategy that included esterification in an initial stage was investigated. Methods for constructing trans-Pro(3-OH) were examined using a convertible isocyanide, which could be converted to a carboxylic acid required for the following amidation. Ester bond formation was achieved through an intermolecular coupling using a hydroxyl-Asp derivative and the corresponding alcohol, and the amidation afforded a linear depsipeptide. The macrolactamization of the linear peptide gave the cyclic depsipeptide, and then the global deprotection accomplished the total synthesis of 1 and its dideoxy derivative.

In Silico Design and Enantioselective Synthesis of Functionalized Monocyclic 3-Amino-1-carboxymethyl-β-lactams as Inhibitors of Penicillin-Binding Proteins of Resistant Bacteria

As a complement to the renowned bicyclic β-lactam antibiotics, monocyclic analogues provide a breath of fresh air in the battle against resistant bacteria. In that framework, the present study discloses the in silico design and unprecedented ten-step synthesis of eleven nocardicin-like enantiomerically pure 2-{3-[2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoazetidin-1-yl}acetic acids starting from serine as a readily accessible precursor. The capability of this novel class of monocyclic 3-amino-β-lactams to inhibit penicillin-binding proteins (PBPs) of various (resistant) bacteria was assessed, revealing the potential of α-benzylidenecarboxylates as interesting leads in the pursuit of novel PBP inhibitors. No deactivation by representative enzymes belonging to the four β-lactamase classes was observed, while weak inhibition of class C β-lactamase P99 was demonstrated.

Improved preparation method of modified lacosamide

The invention discloses an improved preparation method of modified lacosamide, which is simple to operate, high in chiral purity and low in cost. According to the improved preparation method, in step 1, amidation is carried out on amino by utilizing di-tert butyl dicarbonate (Boc for short), wherein conditions are moderate and the chiral purity is high and at least reaches 90 percent or more; in step 4, high-selectivity dimethyl sulfate is used as a methylation reagent; the cost is low and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application. The improved preparation method has the most important innovation points that the Boc is used as an N-protection agent and a Boc protecting group can be simply and conveniently removed by adding acid and a hydrogenation removal means does not need to be used. Secondly, the low-price dimethyl sulfate is used for carrying out methylation and the conditions are moderate; the methylation yield is high and the improved preparation method is more suitable for large-scale application.

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.

Gold-silver catalyzed straightforward one pot synthesis of pyrano[3,4-: B] pyrrol-7(1 H)-ones

Pyrano[3,4-b]pyrrol-7(1H)-one is a bicyclic structure that is rarely described in the literature but is found in numerous polycyclic natural products as lamellarins. This work presents a one-pot synthesis of pyrano[3,4-b]pyrrol-7(1H)-one substituted in the 2- and 5-position. The reaction proceeds via a one-pot two step 5-endo-dig and 6-endo-dig cyclization catalyzed by a cationic gold complex with high regioselectivity.

New reagent for the introduction of Boc protecting group to amines: Boc-OASUD

A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.