34582-32-6

Basic information

• Product Name: Boc-Asp-OtBu
• Synonyms: N-[[(tert-Butyl)oxy]carbonyl]-L-aspartic acid 4-(tert-butyl) ester;(2S)-2-(tert-Butoxycarbonylamino)succinic acid 1-tert-butyl ester;N-(tert-Butoxycarbonyl)-L-aspartic acid 1-tert-butyl ester;N-tert-Butoxycarbonyl-L-aspartic acid 1-tert-butyl ester;5-BOC-Asp-Ot Bu;N-tert-Boc-L-aspartic Acid tert-Butyl Ester;N-(tert-Butoxycarbonyl)aspartic Acid α-tert-Butyl Ester;N-[(1,1-DiMethylethoxy)carbonyl]-L-aspartic Acid 1-(1,1-DiMethylethyl) Ester
• CAS NO: 34582-32-6
• Molecular Formula: C₁₃H₂₃NO₆
• Molecular Weight: 289.32
• EINECS: 1592732-453-0
• Product Categories: Amino Acids & Derivatives;Chiral Reagents;Inhibitors;Amino Acid Derivatives;Aspartic acid [Asp, D];Boc-Amino Acids and Derivative
• Mol File: 34582-32-6.mol

Chemical Properties

• Melting Point: 101-103?C
• Boiling Point: 429.011 °C at 760 mmHg
• Flash Point: 213.259 °C
• Appearance: White/Powder
• Density: 1.139
• Vapor Pressure: 1.46E-08mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: -15°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.13±0.19(Predicted)
• BRN: 4191701
• CAS DataBase Reference: Boc-Asp-OtBu(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-Asp-OtBu(34582-32-6)
• EPA Substance Registry System: Boc-Asp-OtBu(34582-32-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 34582-32-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-Asp-OtBu is used as a building block for the synthesis of various pharmaceutical compounds. Its stereoselective synthesis properties allow for the creation of specific drug molecules with desired chiral configurations, which can significantly impact the effectiveness and safety of the final product.
Used in Chemical Synthesis:
In the chemical synthesis industry, Boc-Asp-OtBu is used as a key intermediate in the production of various chemical compounds. Its unique properties enable the development of new materials with specific characteristics, such as improved stability or enhanced reactivity.
Used in Research and Development:
Boc-Asp-OtBu is also utilized in research and development settings, where it serves as a valuable tool for studying the properties and behavior of aspartic acid derivatives. This knowledge can be applied to the design and development of new drugs, materials, and other chemical products.

InChI:InChI=1/C13H23NO6/c1-12(2,3)19-10(17)8(7-9(15)16)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,15,16)/t8-/m0/s1

Upstream product

• 126181-44-0 2-Amino-succinic acid 1-tert-butyl ester 4-methyl ester 
• 80963-08-2 N-tert-butoxycarbonyl-L-aspartic acid β-benzyl α-tert-butyl diester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 540-88-5 acetic acid tert-butyl ester 
• 104072-49-3 L-aspartic acid α-t-butyl β-methyl diester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 94347-11-2 4-benzyl 1-t-butyl L-aspartate 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 34582-31-5 1-tert-butyl 4-methyl (S)-2-{[(tert-butoxy)carbonyl]amino}butanedioate 

Downstream Products

• 132018-90-7 N-Boc-L-aspartic acid α-tert-butyl β-6-nitroveratryl diester 
• 81323-58-2 N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester 
• 269733-15-5 (S)-5-tert-Butoxycarbonylamino-2-(triphenylphosphoranylidene)-3-oxohexanedioic acid di-tert-butyl ester 
• 2387-23-7 1,3-Dicyclohexylurea 
• 186534-36-1 Asparic acid 2-hydroxyethylthioethyl ester 
• 592532-11-1 4-(4-benzyloxycarbonylamino-4-methoxycarbonyl-butyrylperoxy)-2-tert-butoxycarbonylamino-4-oxo-butyric acid tert-butyl ester 
• 592532-10-0 4-(4-benzyloxycarbonyl-4-benzyloxycarbonylamino-butyrylperoxy)-2-tert-butoxycarbonylamino-4-oxo-butyric acid tert-butyl ester 
• 163210-89-7 tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate 
• 653589-10-7 1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate 
• 874770-90-8 2-tert-butoxycarbonylamino-succinic acid 1-tert-butyl ester 4-[6-methoxy-2-(4-methoxy-phenyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester 

Relevant articles and documents

Synthesis of meta-Carboranyl-(S)-homocysteine Sulfoxide

New (S)-homocysteine derivatives containing a meta-carborane fragment were synthesized. m-Carboranyl-(S)-homocysteine sulfoxide was obtained as a mixture of diastereoisomers. The reduction of the side-chain carboxy group of N-tert-butoxycarbonyl-(S)-aspartic acid α-tert-butyl ester with sodium tetrahydridoborate was not accompanied by racemization.

Improved enantioselective gram scale synthesis route to N-Fmoc-protected monofluoroethylglycine

Fluorine, as a substituent in amino acids, has found its way into peptide and protein engineering. The basis for the use of this valuable tool is the synthetic accessibility of various fluorinated amino acids as building blocks of peptides and proteins. In this context, we present a straightforward eight-step synthesis of N-Fmoc-L-monofluoroethylglycine (MfeGly) via homoserine (Hse) as intermediate and using various nucleophilic fluorination strategies.

Stereoselective Synthesis of Protected l - Allo -Enduracididine and l -Enduracididine via Asymmetric Nitroaldol Reaction

The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l - allo -enduracididine and l -enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l -aspartic acid. The cyclic guanidine of di-Cbz-protected l - allo -enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.

Process for preparing deuterated desmosine and derivatives thereof

There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.

Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters

Transition-metal-catalyzed transformations of amino acids and peptides could provide a powerful method for their site-selective modification. Here, we report non-decarbonylative Pd-catalyzed Suzuki-Miyaura reactions of phenyl ester derivatives of aspartic acid to form aryl-amino ketones. These products are potentially important in the synthesis of pharmaceuticals, and our methodology represents a new route to access molecules of this type.

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

Synthesis of ortho-carboranyl derivatives of (S)-asparagine and (S)-glutamine

(S)-Asparagine and (S)-glutamine ortho-carboranyl derivatives with free amino and carboxy groups in the α-position were synthesized. By an example of Nγ-(1,2-dicarba-closo-dodecarboran-3-yl)-(S)-glutamine it was demonstrated that the developed synthetic approach carboranyl derivatives of amino acids allowed the preparation of optically pure isomers.

Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups

Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.

[18F](2S,4S)-4-(3-Fluoropropyl)glutamine as a tumor imaging agent

Although the growth and proliferation of most tumors is fueled by glucose, some tumors are more likely to metabolize glutamine. In particular, tumor cells with the upregulated c-Myc gene are generally reprogrammed to utilize glutamine. We have developed new 3-fluoropropyl analogs of glutamine, namely [18F](2S,4R)- and [18F](2S,4S)-4-(3-fluoropropyl)glutamine, 3 and 4, to be used as probes for studying glutamine metabolism in these tumor cells. Optically pure isomers labeled with 18F and 19F (2S,4S) and (2S,4R)-4-(3-fluoropropyl)glutamine were synthesized via different routes and isolated in high radiochemical purity (>95%). Cell uptake studies of both isomers showed that they were taken up efficiently by 9L tumor cells with a steady increase over a time frame of 120 min. At 120 min, their uptake was approximately two times higher than that of L-[3H]glutamine ([3H]Gln). These in vitro cell uptake studies suggested that the new probes are potential tumor imaging agents. Yet, the lower chemical yield of the precursor for 3, as well as the low radiochemical yield for 3, limits the availability of [18F](2S,4R)-4-(3-fluoropropyl)glutamine, 3. We, therefore, focused on [18F](2S,4S)-4-(3-fluoropropyl)glutamine, 4. The in vitro cell uptake studies suggested that the new probe, [18F](2S,4S)-4-(3-fluoropropyl)glutamine, 4, is most sensitive to the LAT transport system, followed by System N and ASC transporters. A dualisotope experiment using L-[3H]glutamine and the new probe showed that the uptake of [3H]Gln into 9L cells was highly associated with macromolecules (>90%), whereas the [18F](2S,4S)-4-(3-fluoropropyl)glutamine, 4, was not (18F](2S,4S)-4-(3-fluoropropyl)glutamine, 4, may be useful for testing tumors that may metabolize glutamine related amino acids.