71460-15-6

Basic information

• Product Name: (R)-2-Amino-4-pentynoic acid t-butyl ester
• Synonyms: (R)-2-Amino-4-pentynoic acid t-butyl ester;tert-Butyl (2S)-2-Amino-4-pentynoate HCl
• CAS NO: 71460-15-6
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.2209
• Product Categories: API intermediates
• Mol File: 71460-15-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 233.343 °C at 760 mmHg
• Flash Point: 99.853 °C
• Appearance: /
• Density: 1.005 g/cm³
• CAS DataBase Reference: (R)-2-Amino-4-pentynoic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Amino-4-pentynoic acid t-butyl ester(71460-15-6)
• EPA Substance Registry System: (R)-2-Amino-4-pentynoic acid t-butyl ester(71460-15-6)

Safety Data

• Hazardous Substances Data: 71460-15-6(Hazardous Substances Data)

Usage

General Description

The chemical (R)-2-Amino-4-pentynoic acid t-butyl ester is a compound that consists of a pentynoic acid attached to a t-butyl ester functional group and an amino group in the R configuration. It has a molecular formula of C9H15NO2 and a molecular weight of 169.22 g/mol. (R)-2-Amino-4-pentynoic acid t-butyl ester is used in organic synthesis and pharmaceutical research as a building block for the synthesis of various molecules and pharmaceutical compounds. Its t-butyl ester functional group makes it more stable and easier to handle in chemical reactions, and its amino group allows it to participate in various types of chemical reactions and form new compounds.

Upstream product

• 326667-54-3 tert-butyl (S)-2-[(diphenylmethylene)amino]pent-4-ynoate 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 540-88-5 acetic acid tert-butyl ester 
• 23235-01-0 (2S)-2-amino-4-pentynoic acid 
• 23235-02-1 N-Acetyl-α-propargylglycine 
• 50428-03-0 D,L-propargylglycine 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 115-11-7 isobutene 
• 23235-01-0 (R)-2-aminopent-4-ynoic acid 

Downstream Products

• 198561-07-8 Fmoc-L-propargyl-Gly-OH 
• 1332640-94-4 C₁₅H₁₇N₃O₇S 
• 1332641-05-0 C₁₂H₁₂N₂O₆S 
• 1332641-04-9 C₁₆H₂₀N₂O₆S 
• 1019996-20-3 C₁₅H₁₈N₂O₆S 

Relevant articles and documents

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.

A practical aryl unit for azlactone dynamic kinetic resolution: Orthogonally protected products and a ligation-inspired coupling process

The first strategy for bringing about enantioselective azlactone dynamic kinetic resolution to generate orthogonally protected amino acids has been developed. In the presence of a C2-symmetric squaramide-based catalyst, benzyl alcohol reacts with novel yet readily prepared tetrachloroisopropoxycarbonyl-substituted azlactones to generate trapped phthalimide products of significant synthetic interest with excellent enantiocontrol. These materials are masked amino acids which are demonstrably orthogonally protected: cleavage of the phthalimide can be achieved in the presence of the ester and vice versa. This process could be utilized to bring about a highly stereoselective ligation-type coupling of protected serines (at stoichiometric loadings) with racemic azlactones derived from both natural and abiotic amino acids. After deprotection, a subsequent base-mediated Oa??N acyl transfer occurs to form a dipeptide.

Structural permutation of potent cytotoxin, polytheonamide B: Discovery of cytotoxic peptide with altered activity

Polytheonamide B (1) is an ion-channel forming natural peptide with a d,l-alternating 48 amino acid sequence, which is an exceedingly potent cytotoxin. We recently designed and synthesized a simplified dansylated polytheonamide mimic 2, in which six amino