82010-31-9

Basic information

• Product Name: BOC-L-LEUCINOL
• Synonyms: BOC-(S)-2-AMINO-4-METHYL-1-PENTANOL;BOC-LEUCINOL;BOC-LEU-OL;BOC-L-LEUCINOL;BOC-L-LEU-OL;(S)-2-(TERT-BUTYLOXYCARBONYL-AMINO)-4-METHYL-1-PENTANOL;(S)-(-)-2-(BOC-AMINO)-4-METHYL-1-PENTANOL;N-T-BOC-L-LEUCINOL
• CAS NO: 82010-31-9
• Molecular Formula: C₁₁H₂₃NO₃
• Molecular Weight: 217.31
• Product Categories: Amino Acids;Leucine [Leu, L];Amino Alcohols;Boc-Amino acid series;Amino Acid Derivatives;Amino Alcohols;Peptide Synthesis
• Mol File: 82010-31-9.mol

Chemical Properties

• Boiling Point: 213 °C
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow/Viscous Liquid
• Density: 0.983
• Vapor Pressure: 2.8E-05mmHg at 25°C
• Refractive Index: n20/D 1.450
• Storage Temp.: -15°C
• PKA: 12.11±0.46(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 4178460
• CAS DataBase Reference: BOC-L-LEUCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-LEUCINOL(82010-31-9)
• EPA Substance Registry System: BOC-L-LEUCINOL(82010-31-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 82010-31-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H23NO3/c1-8(2)6-9(7-13)12-10(14)15-11(3,4)5/h8-9,13H,6-7H2,1-5H3,(H,12,14)/t9-/m0/s1

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 543-27-1 isobutyl chloroformate 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 1234196-13-4 2-(tert-butoxycarbonylamino)-4-methylpentyl acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 34619-03-9 tert-butyldicarbonate 
• 61-90-5 L-leucine 
• 2666-93-5 (S)-Leu-OMe 
• 25462-20-8 2-hydroxymethyl-4-methylpentan-1-ol 
• 39520-24-6 Isobutylmalonsaeure-dimethylester 
• 913546-31-3 (S)-2-(acetyloxymethyl)-4-methylpentanoic acid 
• 14568-42-4 (S)-2-isocyanato-4-methylpentyl acetate 
• 913546-29-9 (R)-2-hydroxymethyl-4-methylpentyl acetate 

Downstream Products

• 58521-45-2 tert-butoxycarbonyl-L-leucinal 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 832104-28-6 (S)-2-amino-4-methylpentyl 2-sulfobenzoate 
• 854402-91-8 (3S)-3-Amino-2-hydroxy-5-methyl-N-(2-phenoxyethyl)hexanamide hydrochloride 
• 3392-09-4 Boc-Leu-ONSu 
• 97920-15-5 4(S)-<<<-N^im-tosyl-L-histydyl>amino>-2,2-difluoro-6-methyl-3-oxoheptanoyl>-L-isoleucyl-2-pyridylmethylamine 
• 97920-14-4 {(S)-1-[(S)-1-[(S)-1-(2,2-Difluoro-2-{(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butylcarbamoyl}-acetyl)-3-methyl-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 97995-52-3 {(S)-1-[(S)-1-[(S)-1-((S)-2,2-Difluoro-1-hydroxy-2-{(1S,2S)-2-methyl-1-[(pyridin-2-ylmethyl)-carbamoyl]-butylcarbamoyl}-ethyl)-3-methyl-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 97920-12-2 <4(S)-<<-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine 
• 103346-52-7 <4(S)-<im-tosyl-L-histidyl>amino>-2,2-difluoro-3(R)-hydroxy-6-methylheptanoyl>-L-isoleucyl-2-pyridylmethylamine 
• 82252-38-8 N^α-Boc-LeuΨVal-OBzl 
• 112157-33-2 (H-Leu(CH₂S)-)2*2HCl 
• 142554-62-9 (S)-(-)-1,1-dimethylethyl <3-methyl-1-<<<<<2,6-bis(1-methylethyl)phenyl>amino>carbonyl>amino>methyl>butyl>carbamate 

Relevant articles and documents

COMPOUNDS AND METHODS OF USE

Disclosed are heterocyclic compounds or their pharmaceutically acceptable salts with ferroptosis-inducing activity, Those compounds or their pharmaceutically acceptable salts can be used to treat cancer.

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Structure Determination, Biosynthetic Origin, and Total Synthesis of Akazaoxime, an Enteromycin-Class Metabolite from a Marine-Derived Actinomycete of the Genus Micromonospora

A new enteromycin-class antibiotic, akazaoxime (1), possessing an aldoxime functionality in place of O-methyl nitronic acid, was isolated from the cultured extract of a marine-derived actinomycete of the genus Micromonospora, along with known A-76356 (2). The structure of 1, including the absolute stereochemistry of three chiral centers, was established by comprehensive analysis of nuclear magnetic resonance (NMR) and mass spectrometry data coupled with magnetic anisotropy analysis of its phenylglycine methyl ester derivatives. The stereochemistry of 2, not determined previously, was proven to be the same as that of 1 on the basis of the similarity of their NMR and specific rotation data. Precursor feeding experiments using 13C-labeled compounds elucidated that the carbon skeletons of 1 and 2 are constructed from propionate (methylmalonate), leucine, and glycine. Establishment of the concise and flexible synthetic route to 1 enabled us to implement biological evaluation of 1 and its unnatural analogues, demonstrating weak to moderate antimicrobial activities of 1 against Gram-positive Kocuria rhizophila [minimum inhibitory concentration (MIC) of 50 μg/mL] and those of synthetic analogues against a plant pathogen Glomerella cingulata (MIC of 50 μg/mL) and a human pathogen Trichophyton rubrum (MIC of 25-50 μg/mL).

Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.

Urea based foldamers

N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.

Asymmetric 1,4-Addition Reactions Catalyzed by N-Terminal Thiourea-Modified Helical l-Leu Peptide with Cyclic Amino Acids

N-terminal thiourea-modified l-Leu-based peptide {(3,5-diCF3Ph)NHC(=S)-(l-Leu-l-Leu-Ac5c)2-OMe} with five-membered ring α,α-disubstituted α-amino acids (Ac5c) catalyzed a highly enantioselective 1,4-addition reaction between β-nitrostyrene and dimethyl malonate. The enantioselective reaction required only 0.5 mol % chiral peptide-catalyst in the presence of iPr2EtN (2.5 equiv.), and gave a 1,4-adduct with 93 % ee of an 85 % yield. As Michael acceptors, various β-nitrostyrene derivatives such as methyl, p-fluoro, p-bromo, and p-methoxy substituents on the phenyl group, 2-furyl, 2-thiophenyl, and naphthyl β-nitroethylenes could be applied. Furthermore, various alkyl malonates and cyclic β-keto-esters could be used as Michael donors. It became clear that the length of the peptide chain, a right-handed helical structure, amide N?Hs, and the N-terminal thiourea moiety play crucial roles in asymmetric induction.

Vinyl sulfone-based inhibitors of trypanosomal cysteine protease rhodesain with improved antitrypanosomal activities

The number of reported cases of Human African Trypanosmiasis (HAT), caused by kinetoplastid protozoan parasite Trypanosoma brucei, is declining in sub-Saharan Africa. Historically, such declines are generally followed by periods of higher incidence, and one of the lingering public health challenges of HAT is that its drug development pipeline is historically sparse. As a continuation of our work on new antitrypanosomal agents, we found that partially saturated quinoline-based vinyl sulfone compounds selectively inhibit the growth of T. brucei but displayed relatively weak inhibitory activity towards T. brucei's cysteine protease rhodesain. While two nitroaromatic analogues of the quinoline-based vinyl sulfone compounds displayed potent inhibition of T. brucei and rhodesain. The quinoline derivatives and the nitroaromatic-based compounds discovered in this work can serve as leads for ADME-based optimization and pre-clinical investigations.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.