79069-14-0

Basic information

• Product Name: N-Boc-L-Valinol
• Synonyms: BOC-(S)-2-AMINO-3-METHYL-1-BUTANOL;BOC-VAL-OL;BOC-VALINOL;BOC-L-VAL-OL;BOC-L-VALINOL;(R)-2-BOC-3-METHYL-1-BUTANOL;(S)-N-(TERT-BUTOXYCARBONYL)VALINOL;(S)-(-)-BOC-VALINOL
• CAS NO: 79069-14-0
• Molecular Formula: C₁₀H₂₁NO₃
• Molecular Weight: 203.28
• Product Categories: Amino Acids;Amino Alcohols;Chiral Compound;Boc-Amino acid series;Amino Acid Derivatives;Amino Alcohols;Peptide Synthesis
• Mol File: 79069-14-0.mol

Chemical Properties

• Boiling Point: 208 °C(lit.)
• Flash Point: 185 °F
• Appearance: /
• Density: 0.995 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.15E-05mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Store at 0-5°C
• PKA: 12.02±0.46(Predicted)
• BRN: 4663728
• CAS DataBase Reference: N-Boc-L-Valinol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-L-Valinol(79069-14-0)
• EPA Substance Registry System: N-Boc-L-Valinol(79069-14-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 79069-14-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-L-Valinol is used as a starting material for the synthesis of enantiopure homo-β-amino acids, which are essential components in the development of pharmaceuticals with improved selectivity and potency.
Used in Organic Synthesis:
N-Boc-L-Valinol is used as an intermediate in the efficient synthesis of enantiopure tetrahydroisoquinolines, which are important scaffolds in the design of bioactive molecules and pharmaceutical agents.
Used in Chemical Research:
N-Boc-L-Valinol is used as an intermediate in the one-pot conversion of amino acid carbamates to N-derivatized 2-oxazolidinones, a process that simplifies the synthesis of complex organic molecules and contributes to the advancement of chemical research.

InChI:InChI=1/C10H21NO3/c1-7(2)8(6-12)11-9(13)14-10(3,4)5/h7-8,12H,6H2,1-5H3,(H,11,13)/t8-/m1/s1

Upstream product

• 3392-12-9 Boc-Val-ONSu 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72-18-4 L-valine 
• 2026-48-4 (S)-valinol 
• 79069-51-5 (S)-N-tert-butoxycarbonylvalinal 
• 4276-09-9 (R)-2-amino-3-methylbutanol 
• 640-68-6 D-Val-OH 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 22838-58-0 Boc-D-Val-OH 
• 142618-88-0 (4R, 5S)-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-4-isopropyl-2-oxazolidinone 
• 402741-10-0 (4R,5S)-5-acetyl-4-isopropyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 306776-30-7 (1R,2S)-(2,3-dihydroxy-1-isopropyl-3-methylbutyl)carbamic acid tert-butyl ester 
• 402741-12-2 (4R,5S)-5-acetyloxy-4-isopropyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 1073176-29-0 (S)-tert-butyl 3-methyl-1-(2-nitro-4-(trifluoromethyl)phenoxy)butan-2-ylcarbamate 
• 1361509-85-4 Boc-Valψ[CH2N(Nos)]Gly-OEt 
• 1449127-77-8 C₃₅H₄₂N₂O₅ 
• 1449127-66-5 C₃₁H₃₄N₂O₅ 
• 1449127-69-8 C₄₇H₈₁N₉O₈ 
• 146476-35-9 (1S)-[1-[(diphenylphosphino)methyl]-2-methylpropyl]carbamic acid 1,1-dimethylethyl ester 
• 263024-64-2 Acetic acid (1R,2R)-2-acetoxy-1,2-bis-{(S)-1-[(diphenylphosphanyl)-methyl]-2-methyl-propylcarbamoyl}-ethyl ester 
• 263024-62-0 (R,R)-2,2-dimethyl-1,3-dioxolane-4,5-diacid-bis{[(1'S)-1'-(diphenylphosphinomethyl)-2'-methyl-propyl]amide} 
• 263024-60-8 (S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)oxaldiamide 
• 146476-37-1 (2S)-1-(diphenylphosphino)-3-methylbutan-2-amine 
• 293305-73-4 tert-butyl (1R)-1,2-dimethylpropyl carbamate 
• 758-27-0 (R)-1,2-dimethylpropylamine hydrochloride 

Relevant articles and documents

Structural Basis for α-Helix Mimicry and Inhibition of Protein–Protein Interactions with Oligourea Foldamers

Efficient optimization of a peptide lead into a drug candidate frequently needs further transformation to augment properties such as bioavailability. Among the different options, foldamers, which are sequence-based oligomers with precise folded conformation, have emerged as a promising technology. We introduce oligourea foldamers to reduce the peptide character of inhibitors of protein–protein interactions (PPI). However, the precise design of such mimics is currently limited by the lack of structural information on how these foldamers adapt to protein surfaces. We report a collection of X-ray structures of peptide–oligourea hybrids in complex with ubiquitin ligase MDM2 and vitamin D receptor and show how such hybrid oligomers can be designed to bind with high affinity to protein targets. This work should enable the generation of more effective foldamer-based disruptors of PPIs in the context of peptide lead optimization.

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.

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.

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.

Enantio- And regioselective asymmetric allylic substitution using a chiral aminophosphinite ruthenium complex: an experimental and theoretical investigation

The design and synthesis of a new chiral aminophosphinite-ligated ruthenium complex is described. The ruthenium complex, [Ru(AMP)2(CH3CN)2][BPh4]2{AMP = (S)-tert-butyl 1-(diphenylphosphinooxy)-3-methylbutan-2-ylcarbamate}, has been found to catalyze nucleophilic addition of phenol and carboxylic acid to allyl chloride in a highly regioselective fashion with enantiomeric excess ranging from 12 to 90.

N-1 BRANCHED ALKYL ETHER SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS, COMPOSITIONS, AND METHODS

Imidazo[4,5-c]quinoline compounds having a substituent that is attached at the N-1 position by a branched group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in humans and animals, and in the treatment of diseases including infectious and neoplastic diseases are also disclosed.

N-1 BRANCHED ALKYL SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS, COMPOSITIONS, AND METHODS

Imidazo[4,5-c]quinoline compounds having a substituent that is attached at the N-1 position by a branched group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing (or inhibiting) cytokine biosynthesis in humans and animals, and in the treatment of diseases including infectious and neoplastic diseases are also disclosed.

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups

Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.