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(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid is an amino acid derivative characterized by a unique molecular structure with a 2R,3S configuration. It features a tert-butoxycarbonylamino group at the third carbon, a hydroxy group at the second carbon, and a phenyl group at the fourth carbon. (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid may be employed in various chemical reactions and synthesis processes, particularly in the pharmaceutical and drug development industries.

105181-72-4

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105181-72-4 Usage

Uses

Used in Pharmaceutical and Drug Development Industry:
(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique molecular structure and stereoisomeric arrangement make it a valuable building block for the development of new drugs with potential therapeutic applications.
(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid is also used as a chiral auxiliary in asymmetric synthesis, enabling the production of enantiomerically pure compounds. This is crucial in the pharmaceutical industry, as the biological activity and safety of chiral drugs can be significantly influenced by their stereochemistry.
Furthermore, (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid may be utilized in the development of novel drug delivery systems, such as nanoparticles or polymeric carriers, to improve the bioavailability and therapeutic efficacy of various pharmaceutical agents.

Check Digit Verification of cas no

The CAS Registry Mumber 105181-72-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,5,1,8 and 1 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 105181-72:
(8*1)+(7*0)+(6*5)+(5*1)+(4*8)+(3*1)+(2*7)+(1*2)=94
94 % 10 = 4
So 105181-72-4 is a valid CAS Registry Number.

105181-72-4Downstream Products

105181-72-4Relevant articles and documents

Synthesis of di- and tripeptide analogues containing α-ketoamide as a new core structure for inhibition of HIV-1 protease

Sheha, Mahmoud M.,Mahfouz, Nadia M.,Hassan, Hoda Y.,Youssef, Adel F.,Mimoto, Tsutomu,Kiso, Yoshiaki

, p. 887 - 894 (2000)

Di- and tripeptide analogues containing α-ketoamide as a new core structure and incorporating allophenylnorstatine (Apns) as a transition state mimic, were designed and synthesized in the hope of obtaining a novel structural type of HIV-1 protease inhibitors. The immediate precursor, Apns-Thz-NHBu(t) was prepared by coupling of Boc-Apns with N-tert·butyl Thz-4-carboxamide hydrochloride. Removal of Boc group followed by coupling with the respective α-ketoacid residue (P2) gave the desired dipeptides (8-12) in almost quantitative yields. The α-keto tripeptides (18-21) were obtained by oxidation of the hydroxyl group of Apns (PI) in the appropriate tripeptide, iQOA-Val-Apns-(un)substituted Thz(Oxa)-NHBu1 with DMSO/DCC. Preliminary evaluation of the activity of the synthesized derivatives was determined as percentage of enzyme inhibition at 5 μM and 50 nM levels of the di- and tripeptides respectively. The α-ketoamides displayed a significant enhanced potency relative to their parent isosteres as inhibitors of HIV-1 protease and are shown to be a promising new core structure for the development of enzyme inhibitors. A quantitative approach was attempted, using an LFE model, correlating the effect of structural modification and HIV-1 protease inhibition activity of the prepared dipeptides. The result indicates the contribution of the torsion angle by 84% to the activity of the inhibitors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Design and synthesis of several small-size HTLV-I protease inhibitors with different hydrophilicity profiles

Nguyen, Jeffrey-Tri,Kato, Keiko,Hidaka, Koushi,Kumada, Henri-Obadja,Kimura, Tooru,Kiso, Yoshiaki

supporting information; experimental part, p. 2425 - 2429 (2011/06/17)

The human T cell leukemia/lymphotropic virus type 1 (HTLV-I) is clinically associated with adult T cell leukemia/lymphoma, HTLV-I associated myelopathy/tropical spastic paraparesis, and a number of other chronic inflammatory diseases. To stop the replication of the virus, we developed highly potent tetrapeptidic HTLV-I protease inhibitors. In a recent X-ray crystallography study, several of our inhibitors could not form co-crystal complexes with the protease due to their high hydrophobicity. In the current study, we designed, synthesized and evaluated the HTLV-I protease inhibition potency of compounds with hydrophilic end-capping moieties with the aim of improving pharmaceutic and pharmacokinetic properties.

A practical and convenient synthesis of the protease inhibitor epibestatin

Richter, Anja,Hedberg, Christian

experimental part, p. 2039 - 2042 (2010/08/13)

A convenient synthesis of the protease inhibitor epibestatin, a useful component in protease inhibition cocktails for use in proteomics research, is described. The synthesis sequence consists of seven steps, starting from phenylacetaldehyde, yielding enantiopure epibestatin in 8% overall yield. A regioselective Mitsunobu transformation of a diol is the key step in the sequence. Georg Thieme Verlag Stuttgart.

PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND

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Page 14, (2008/06/13)

The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare oxazolidinone derivatives of β-hydroxyethylamine compounds having an inverted steric configuration at the β

Design and synthesis of broad-based mono- and bi- cyclic inhibitors of FIV and HIV proteases

Mak, Chi Ching,Brik, Ashraf,Lerner, Danica L.,Elder, John H.,Morris, Garrett M.,Olson, Arthur J.,Wong, Chi-Huey

, p. 2025 - 2040 (2007/10/03)

Based on the substrate transition state and our strategy to tackle the problem of drug resistance, a series of HIV/FIV protease (HIV/FIV PR) monocyclic inhibitors incorporating a 15- or 17-membered macrocycle with an equivalent P3 or P3′ group and a uniqu

Application of the lewis acid-lewis base bifunctional asymmetric catalysts to pharmaceutical syntheses: Stereoselective chiral building block syntheses of human immunodeficiency virus (HIV) protease inhibitor and β3- adenergic receptor agonist

Nogami, Hiroyuki,Kanai, Motomu,Shibasaki, Masakatsu

, p. 702 - 709 (2007/10/03)

Chiral building block syntheses of promising drugs were achieved using two types of catalytic stereoselective cyanosilylations of aldehydes promoted by Lewis acid-Lewis base bifunctional catalysts 1 and 2 as the key steps (diastereoselective cyanosilylation of amino aldehyde and enantioselective cyanosilylation). In the first part of this article, syntheses of chiral building blocks (6) of Atazanavir (3: human immunodeficiency virus (HIV) protease inhibitor) using the bifunctional catalyst 2 are discussed. The reaction of Boc-protected phenylalaninal 21 in the presence of 1 mol% catalyst 2 selectively afforded the anti isomer 22 as the major product (diastereomeric ratio=97:3), which was successively converted to the corresponding epoxide 6 in six steps. In the second part, we describe a chiral building block synthesis of β3-adrenergic receptor agonists. The enantioselective cyanosilylation of 3-chlorobenzaldehyde (38) with 9 mol% catalyst 1 gave the chiral cyanohydrin 39, which was converted to β-hydroxyethylamine 40 by reduction. Moreover, the chiral ligand of catalyst 1 could be recovered without column chromatography and reused without decreasing its activity.

PROCESS FOR PRODUCING 3-AMINO-2-HYDROXYPROPIONIC ACID DERIVATIVES

-

, (2008/06/13)

The present invention provides a process for preparing 3-amino-2-hydroxypropionic acid derivatives (1) which does not use dangerous reagents, is economically advantageous, and is suitable for an industrial production, which process comprises:treating N-protected-3-amino-2-hydroxypropionic acid derivatives (2) having a steric configuration at 2-position carbon reverse to that of derivatives (1) with a leaving group-introducing agent to convert into N-protected-3-aminopropionic acid derivatives (3),then treating the derivatives with a basic substance to convert into substituted-3-amino-2-hydroxypropionic acid derivatives (4) having an inverted steric configuration at 2-position carbon,and then converting the derivatives into 3-amino-2-hydroxypropionic acid derivatives (1).

Production method of beta-amino-alpha-hydroxycarboxylic acid

-

, (2008/06/13)

The present invention provides a production method of an optically active β-amino-α-hydroxycarboxylic acid, which includes the following steps (a)-(c): (a) treating an optically active N-carbamate protected β-amino epoxide with an acid to give an optically active 5-hydroxymethyl-2-oxazolidinone; (b) oxidizing the resulting compound in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an optically active 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid; and (c) treating the 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid with a base, and a production method of an optically active N-carbamate protected β-amino-α-hydroxycarboxylic acid which includes protection of the amino group with a carbamate type protecting group. The industrial production method of the present invention can produce these compounds efficiently.

Process for producing alpha-aminoketone derivatives

-

, (2008/06/13)

A process for producing α-amino-dihalogenated methyl ketone derivatives by reacting an N-protected α-amino acid ester with a dihalomethyl lithium is provided. This process is suitable for the production on an industrial scale and by this process, α-amino-

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Ikunaka, Masaya,Matsumoto, Jun,Nishimoto, Yukifumi

, p. 1201 - 1208 (2007/10/03)

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.

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