13795-73-8

Usage

Uses

Used in Organic Synthesis:
(2S)-2-Aminobutanedioic acid ditert-butyl ester is used as a reagent in organic synthesis for its ability to protect the amino group of serine during chemical reactions. This protection allows for selective reactions to occur at other sites on the molecule, facilitating the synthesis of complex organic compounds.
Used in Pharmaceutical Intermediates:
In the pharmaceutical industry, (2S)-2-Aminobutanedioic acid ditert-butyl ester serves as a key building block for the development of various drugs. Its protected structure enables the creation of novel drug candidates with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Biochemical Research:
(2S)-2-Aminobutanedioic acid ditert-butyl ester is utilized in biochemical research as a protected form of serine. This allows researchers to study the role of serine in biological systems and enzymatic reactions without the complications of unwanted side reactions, thus enhancing the understanding of serine's biological functions and its potential applications in medicine.

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 56-84-8 L-Aspartic acid 
• 1152-61-0 N-Cbz-L-Asp 
• 4219-41-4 β-tert.-butyl>-L-asparagin-tert.-butylester 
• 115-11-7 isobutene 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 49827-15-8 t-butyl iodoacetate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 42417-76-5 1,4-di-tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}butanedioate 
• 1634-04-4 tert-butyl methyl ether 
• 1791-13-5 L-aspartic acid di-tert-butyl ester hydrochloride 

Downstream Products

• 103777-98-6 N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert.-butylester)-L-asparaginsaeure-di-tert.-butylester 
• 113170-90-4 (S)-di-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)succinate 
• 161878-84-8 (S)-2-((S)-4-tert-Butoxycarbonyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-succinic acid di-tert-butyl ester 
• 131152-68-6 Boc-Tyr-D-Met-Phe-His-Leu-Met-Asp(OBu-t)-OBu-t 
• 1791-13-5 L-aspartic acid di-tert-butyl ester hydrochloride 
• 1131843-87-2 (2S)-2-[((2S*,5S*,7S*,8aR*)-2-allyl-7-benzyloxy-3-oxo-octahydroindolizin-5-ylcarbonyl)amino]succinic acid di(tert-butyl) ester 
• 757241-91-1 N-(2-nitrobenzenesulfonyl)-L-aspartic acid di-t-butyl ester 
• 1147134-18-6 C₂₅H₃₆N₂O₁₀ 
• 1140408-22-5 di-tert-butyl 2-(2-(5-benzyl-6-oxo-3-phenylpyridazin-1(6H)-yl)acetamido)succinate 

Relevant academic research and scientific papers

Synthesis of Silacyclic Dipeptides: Peptide Elongation at Both N-And C-Termini of Dipeptide

A new type of peptide bond formation utilizing silacyclic amino acids or peptides is described. This work has the following advantages: (1) imidazolylsilane is a highly fascinating coupling reagent for dipeptide synthesis from N-,C-Terminal unprotected am

Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum-Polymer Conjugates

(S)-3,4-Dihydroxybutyric acid ((S)-3,4-DHBA), an endogenous straight chain fatty acid, is a normal human urinary metabolite and can be obtained as a valuable chiral biomass for synthesizing statin-class drugs. Hence, its epoxide derivatives should serve as promising monomers for producing biocompatible polymers via alternating copolymerization with carbon dioxide. In this report, we demonstrate the production of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) from racemic-tert-butyl 3,4-epoxybutanoate (rac-tBu 3,4-EB) and CO2 using bifunctional cobalt(III) salen catalysts. The copolymer exhibited greater than 99% carbonate linkages, 100% head-to-tail regioselectivity, and a glass-transition temperature (Tg) of 37 °C. By way of comparison, the similarly derived polycarbonate from the sterically less congested monomer, methyl 3,4-epoxybutanoate, displayed 91.8% head-to-tail content and a lower Tg of 18 °C. The tert-butyl protecting group of the pendant carboxylate group was removed using trifluoroacetic acid to afford poly(3,4-dihydroxybutyric acid carbonate). Depolymerization of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) in the presence of strong base results in a stepwise unzipping of the polymer chain to yield the corresponding cyclic carbonate. Furthermore, the full degradation of the acetyl-capped poly(potassium 3,4-dihydroxybutyrate carbonate) resulted in formation of the biomasses, β-hydroxy-γ-butyrolacetone and 3,4-dihydroxybutyrate, in water (pH = 8) at 37 °C. In addition, water-soluble platinum-polymer conjugates were synthesized with platinum loading of 21.3-29.5%, suggesting poly(3,4-dihydroxybutyric acid carbonate) and related derivatives may serve as platinum drug delivery carriers.

Synthesis of models of the BC ring systems of MPC1001 and MPC1001F

Piperazinedione 13, representing the BC rings of the anti-prostate cancer fungal metabolite MPC1001, was prepared by a route in which a sulfur-stabilized carbanion derived from 22 cyclizes onto the terminal ester of the pendant chain attached to N1. Another model, 14, was synthesized by cyclization of an α-ketoamide nitrogen onto an ester; 14 represents the BC rings of MPC1001F.

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

An efficient synthesis of tert-butyl ethers/esters of alcohols/amino acids using methyl tert-butyl ether

A facile synthesis of a wide variety of tert-butyl ethers and tert-butyl ester derivatives under mild conditions is described. Alcohols etherified with tert-butyl methyl ether as tert-butyl source and solvent, in the presence of sulfuric acid. Many amino acid tert-butyl esters have been synthesized by this procedure. The reaction is simple, inexpensive, easily scaled up, and proceeds without observable racemization. A green method was developed for the deprotection of this group using Amberlite resin IR 120-H as catalyst.

Preparation of protected amino acids

The present invention involves a process for preparing protected amino acids. The process produces a di-tert-butyl amino ester or an N-protected di-tert-butyl amino ester by transesterification of an acidic amino acid or an N-protected acidic amino acid. By-products of the transesterification reaction may be recycled for use as part of the starting material. The N-protected di-tert-butyl amino ester may be hydrogenated to form a di-tert-butyl amino ester, which may subsequently form a di-tert-butyl ester hydrocholride salt.

Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis

In this paper, we describe investigations into the use of cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts for the asymmetric alkylation of a benzophenone-derived glycine-imine. Utility of this process is demonstrated by the enantioselective synthesis of a range of α-amino acid esters.

A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of α-amino acids

A new class of Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts bearing a N-anthracenylmethyl function are presented. These catalysts show high stereocontrol in the asymmetric alkylation of a benzophenone-derived glycine-imine, and application of this process to the enantioselective synthesis of a range of α-amino acid esters (e.e. 67-94%) is investigated.