76985-10-9

Basic information

• Product Name: Boc-3-(2-Naphthyl)-D-alanine
• Synonyms: BOC-NAL(2)-OH;BOC-ALA(2-NAPH)-OH;BOC-ALA(2-NAPHTHYL)-OH;BOC-ALA-BETA-(2-NAPHTHYL)-OH;BOC-BETA-(2-NAPHTHYL)-D-ALANINE;BOC-BETA-(2-NAPHTHYL)-L-ALANINE;BOC-D-3-(2-NAPHTHYL)-ALANINE;BOC-D-2-NAL-OH
• CAS NO: 76985-10-9
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;Alanine [Ala, A];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 76985-10-9.mol

Chemical Properties

• Melting Point: 92-95 °C(lit.)
• Boiling Point: 454.92°C (rough estimate)
• Flash Point: 263.6 °C
• Appearance: off-white granular powder
• Density: 1.2164 (rough estimate)
• Vapor Pressure: 2.58E-11mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), Ethanol (Sparingly), Methanol (Slightly)
• PKA: 3.88±0.30(Predicted)
• BRN: 4200660
• CAS DataBase Reference: Boc-3-(2-Naphthyl)-D-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3-(2-Naphthyl)-D-alanine(76985-10-9)
• EPA Substance Registry System: Boc-3-(2-Naphthyl)-D-alanine(76985-10-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 76985-10-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
Boc-3-(2-Naphthyl)-D-alanine is used as a reagent for the synthesis of Lanreotide trisulfide, a somatostatin analog with potential applications in the treatment of various conditions, including acromegaly and neuroendocrine tumors. It aids in the development of drugs with enhanced somatostatin receptor binding activity, which can be beneficial in managing hormone-related disorders.
2. Used in Structure-Activity Relationship Studies:
Boc-3-(2-Naphthyl)-D-alanine is employed in the preparation and study of arginine-containing tripeptides as MC4 receptor ligands. The MC4 receptor is a crucial target for the development of drugs aimed at treating obesity and related metabolic disorders. By using this compound as a reagent, researchers can better understand the structure-activity relationships of these peptides and design more effective drugs targeting the MC4 receptor.

InChI:InChI=1/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-12-8-9-13-6-4-5-7-14(13)10-12/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/p-1/t15-/m1/s1

Upstream product

• 37439-99-9 (S)-N-acetyl-3-(2-naphthyl)alanine 
• 136015-50-4 2-Acetylamino-2-naphthalen-2-ylmethyl-malonic acid monoethyl ester 
• 172214-89-0 2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63024-44-2 2-Amino-3-naphthalen-2-yl-propionic acid; hydrochloride 
• 6960-34-5 L-3-(2-naphthyl)alanine 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 66-99-9 β-naphthaldehyde 
• 35799-85-0 (R)-N-Acetyl-3-(2-naphthyl)alanine Methyl Ester 
• 68100-02-7 (Z)-2-methyl-4-(naphthalen-2-ylmethylene)oxazol-5(4H)-one 
• 7732-18-5 water 
• 76985-09-6 (R)-2-naphthylalanine 

Downstream Products

• 1187049-71-3 TPI-1345-170 
• 200864-79-5 Boc-D-β-(2-Naphthyl)alanine 2-(4-Hydroxyphenyl)ethylamide 
• 138449-28-2 (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)-N-benzylpropanamide 
• 251308-38-0 [(2-tert-butoxycarbonylamino-3-naphthalen-2-yl-propionyl)-(3-phenyl-propyl)-amino]-acetic acid methyl ester 

Relevant articles and documents

Structure–Activity Relationship Studies on (R)-PFI-2 Analogues as Inhibitors of Histone Lysine Methyltransferase SETD7

SETD7 is a histone H3K4 lysine methyltransferase involved in human gene regulation. Aberrant expression of SETD7 has been associated with various diseases, including cancer. Therefore, SETD7 is considered a good target for the development of new epigenetic drugs. To date, few selective small-molecule inhibitors have been reported that target SETD7, the most potent being (R)-PFI-2. Herein we report structure–activity relationship studies on (R)-PFI-2 and its analogues. A library of 29 structural analogues of (R)-PFI-2 was synthesized and evaluated for inhibition of recombinantly expressed human SETD7. The key interactions were found to be a salt bridge and a hydrogen bond formed between (R)-PFI-2′s NH2+ group and SETD7′s Asp256 and His252 residue, respectively.

ARYLPYRROLIDINE DICARBOXYLIC ACID AMIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a pyrrolidine derivative capable of catalyzing an asymmetric oxidation reaction of an alkene compound. SOLUTION: There is provided an arylpyrrolidine dicarboxylic acid amide derivative exemplified by cat.A in the following formula. There is provided an asymmetric oxidation catalyst having optical purity of 50%. There is provided a manufacturing method of an optically active epoxy compound including contacting the compound with an alkene derivative in addition to a co-oxidant. There is provided a manufacturing method of an optically active epoxy compound, in which the alkene derivative is a substituted alkene derivative having a functional group containing N or O at 3 position of a double bond. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Enantioselective 1,3-dipolar cycloaddition of azomethine imines with propioloylpyrazoles induced by chiral π-cation catalysts

We developed 1,3-dipolar cycloadditions of azomethine imines with propioloylpyrazoles catalyzed by a chiral copper(II) complex of 3-(2-naphthyl)-L-alanine amide. The asymmetric environment created by intramolecular π - cation interaction and the N-alkyl group of the chiral ligand gives the corresponding adducts in high yields with excellent enantioselectivity. This is the first successful method for the catalytic enantioselective 1,3-dipolar cycloaddition of azomethine imines with internal alkyne derivatives to give fully substituted pyrazolines.

Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution

A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity. 2012 Elsevier Ltd.

The preparation of single enantiomer 2-naphthylalanine derivatives using rhodium-methyl BoPhoz-catalyzed asymmetric hydrogenation

The single enantiomers of 2-naphthylalanine and N-tert-butoxycarbonyl 2-naphthylalanine were prepared from 2-naphthaldehyde. The sequence has been optimized and run on multikilogram scale, with the key step the asymmetric hydrogenation of methyl 2-acetamido-3-(2-naphthyl)propenoate using the rhodium complex of the methyl BoPhoz ligand, which proceeded smoothly at scale with 97.9% ee. Enhancement to >99.5% ee was achieved by crystallization of the methyl 2-amino-3-(2-naphthyl)propanoate methanesulfonic acid addition salt, the product of acidic deacylation of the hydrogenation product. This protocol for enantiomeric purity enhancement appears to be general for these types of amino acid derivatives. Subsequent transformations did not effect the enantiomeric purity, affording the desired products in >99.5% ee.

Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds

A highly potent CXCR4 antagonist, compound 2, was previously found by using two orthogonal cyclic pentapeptide libraries involving conformation-based and sequence-based libraries based on the pharmacophore of a 14-mer peptidic antagonist, 1. Herein, cyclic tetrapeptides derived from replacements of the dipeptide unit (Nal-Gly) with a γ-amino acid and pseudopeptides cyclized by disulfide and olefin bridges were synthesized to find novel scaffold structures different from that of cyclic pentapeptides. These compounds contain a reduced number of peptide bonds compared to compound 2. Furthermore, several analogues with chemical modification of the side chain of Arg4 in 2 were also prepared. From these, several new leads possessing high to moderate CXCR4-antagonistic activity were characterized.

Substituted alkyldiamine derivatives

The present invention relates to novel substituted alkyldiamine derivatives and pharmaceutically acceptable salts thereof which are useful tachykinin antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions including asthma, cough, and bronchitis.

Cross-linked crystals of subtilisin: Versatile catalyst for organic synthesis

Cross-linked enzyme crystals (CLECs) of subtilisin exhibit excellent activity in aqueous and various organic solvents. This catalyst is more stable than the native enzyme in both aqueous and mixed aqueous/organic solutions. Subtilisin-CLEC was shown to be a versatile catalyst. It was used for the syntheses of peptides and peptidomimetics, mild hydrolysis of amino acid and peptide amides, enantio- and regioselective reactions, and transesterifications.