105504-72-1

Basic information

• Product Name: N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• Synonyms: N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;BOC-(RS)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;N-Boc-3-hydroxy-DL-valine, 97%;2-((tert-Butoxycarbonyl)aMino)-3-hydroxy-3-Methylbutanoic acid
• CAS NO: 105504-72-1
• Molecular Formula: C10H19NO5
• Molecular Weight: 233.26
• Mol File: 105504-72-1.mol

Chemical Properties

• Boiling Point: 391.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.175±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(105504-72-1)
• EPA Substance Registry System: N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(105504-72-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 105504-72-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a building block for the synthesis of various compounds in pharmaceutical research. Its unique structure allows for the creation of complex molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a key intermediate for the production of a wide range of organic compounds. Its versatility and reactivity make it an essential component in the synthesis of various chemical entities.
Used in Peptide Synthesis:
N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a protected amino acid in peptide synthesis. The BOC protecting group is crucial for preventing unwanted side reactions during the synthesis process, ensuring the formation of the desired peptide sequence.
Used in Drug Development:
In drug development, N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a critical reagent for the synthesis of pharmaceutical intermediates. These intermediates are essential for the production of new drugs, contributing to the advancement of medicinal chemistry.
Used in Chemical and Biochemical Research:
N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a valuable chemical in chemical and biochemical research. Its unique properties and reactivity make it an important tool for studying various chemical and biological processes, contributing to a deeper understanding of the underlying mechanisms.

Upstream product

• 2280-28-6 3-hydroxy-DL-valine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 288159-36-4 tert-butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 75-16-1 methylmagnesium bromide 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 2280-27-5 (S)-2-amino-3-hydroxy-3-methylbutanoic acid 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 34619-03-9 tert-butyldicarbonate 
• 473545-40-3 tert-butyl N-[(1R)-2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]carbamate 
• 1609644-37-2 C₂₀H₂₆N₂O₃ 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 182958-73-2 (2R)-2-(N-tert-Butoxycarbonyl)amino-3-hydroxy-3-methylbutanoic acid 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 473452-22-1 methyl (S)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoate 

Downstream Products

• 473452-26-5 (2S)-2-(N-t-butoxycarbonyl)amino-3-methyl-3-hydroxypropan-1-al 
• 473545-40-3 tert-butyl N-[(1R)-2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]carbamate 
• 182205-76-1 (2R,3R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyryloxy]-3-methyl-pentanoic acid benzyl ester 
• 2280-27-5 (S)-2-amino-3-hydroxy-3-methylbutanoic acid 
• 1275621-77-6 methyl (S)-2-(2,4-dinitrophenylsulfonamido)-3-hydroxy-3-methylbutanoate 
• 1275621-78-7 methyl (S)-1-(2,4-dinitrophenylsulfonyl)-3,3-dimethylaziridine-2-carboxylate 
• 1275621-81-2 (S)-1-(benzhydryloxy)-3-hydroxy-3-methyl-1-oxobutan-2-aminium chloride 
• 1275621-82-3 benzhydryl (S)-2-(2,4-dinitrophenylsulfonamido)-3-hydroxy-3-methylbutanoate 
• 1275621-83-4 benzhydryl (S)-1-(2,4-dinitrophenylsulfonyl)-3,3-dimethylaziridine-2-carboxylate 
• 1275621-84-5 benzhydryl (S)-3,3-dimethylaziridine-2-carboxylate 
• 1422128-71-9 C₂₅H₃₀F₆N₄O₃S 
• 609367-41-1 3-hydroxy-N,N-dimethyl-L-valinamide 
• 1443753-90-9 N-Fmoc (2S)-2-amino-3-(benzyloxyphosphoryloxy)-3-methylbutanoic acid 
• 1443753-95-4 N-Fmoc (2S)-2-amino-3-(dibenzyloxyphosphoryloxy)-3-methylbutanoic acid 

Relevant articles and documents

MONOBACTAM COMPOUNDS AND USE THEREFOR

Monobactam compounds and a use therefor. Specifically provided are chemical compounds represented by formula (I) or isomers, pharmaceutically acceptable salts, solvates, crystals, or prodrugs thereof, preparation methods therefor, pharmaceutical compositions containing said compounds, and a use of said compounds or compositions in treating bacterial infection. The present compounds feature excellent antibacterial activity, and have great hopes of becoming a therapeutic agent for bacterial infection.

Gold-Catalyzed Amide/Carbamate-Linked N, O-Acetal Formation with Bulky Amides and Alcohols

A gold-catalyzed N,O-acetal formation was established to construct an amide/carbamate-linked N,O-acetal substructure with bulky alcohols. The acyliminium cation species generated from o-alkynylbenzoic acid ester in the presence of a gold catalyst is highly reactive and underwent nucleophilic attack of various bulky alcohols and phenols at room temperature under neutral conditions, leading to the corresponding N,O-acetals in yields of 34-89% with good functional group tolerance.

Preparation method of (2S) -substituted -3 - deuterium - L - valdi

The preparation method of the (2S) IV-substituted - deuterium -3 - valine ester compound represented - L - is simple in process. The yield is high, benzene is not needed to be dissolved, the environment is friendly, and the method is suitable for industrialized mass production.

APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY

An application of a compound represented by formula (I) and pharmaceutically acceptable salts thereof in preparation of a drug for treating pneumonia.

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

Disclosed are a class of new monocyclic β-lactam compounds, an isomer thereof or pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compounds, and the use of same in preparing drugs for treating diseases associated

Organic total synthesis method of D-penicillamine

The invention discloses an organic total synthesis method of D-penicillamine, which comprises the following steps: carrying out Grignard reaction on a derivative of Lserine ester and a methyl Grignardreagent to obtain a first intermediate; carrying out oxidation reaction on the first intermediate and an oxidizing agent to obtain a second intermediate; carrying out sulfonylation reaction on the second intermediate and a sulfonylation reagent to obtain a third intermediate; carrying out thiolation reaction on the third intermediate and a vulcanization reagent to obtain a fourth intermediate; and carrying out hydrolysis reaction on the fourth intermediate to obtain the D-penicillamine. The initial raw materials are cheap and easy to obtain, particularly, cheap, easy-to-obtain and high-optical-purity Lserine ester derivatives can be used as the raw materials, the whole synthetic route for preparing the Dapenem is a new organic total synthesis process route, the process is simple, the reaction condition requirement is low, no toxin is left, and the safety performance is good; the product yield and the optical purity are high; and large-scale production is easy to realize.

Optimization of LpxC Inhibitors for Antibacterial Activity and Cardiovascular Safety

UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) is a Zn2+ deacetylase that is essential for the survival of most pathogenic Gram-negative bacteria. ACHN-975 (N-((S)-3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl)-4-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diyn-1-yl)benzamide) was the first LpxC inhibitor to reach human clinical testing and was discovered to have a dose-limiting cardiovascular toxicity of transient hypotension without compensatory tachycardia. Herein we report the effort beyond ACHN-975 to discover LpxC inhibitors optimized for enzyme potency, antibacterial activity, pharmacokinetics, and cardiovascular safety. Based on its overall profile, compound 26 (LPXC-516, (S)-N-(2-(hydroxyamino)-1-(3-methoxy-1,1-dioxidothietan-3-yl)-2-oxoethyl)-4-(6-hydroxyhexa-1,3-diyn-1-yl)benzamide) was chosen for further development. A phosphate prodrug of 26 was developed that provided a solubility of >30 mg mL?1 for parenteral administration and conversion into the active drug with a t1/2 of approximately two minutes. Unexpectedly, and despite our optimization efforts, the prodrug of 26 still possesses a therapeutic window insufficient to support further clinical development.

The journey of total synthesis toward nannocystin Ax

Herein we describe the detail on our full investigations that led to the achievement of the total synthesis of nannocystin Ax, a 21-membered macrocyclic natural product composing of a tripeptide fragment and a polyketide fragment, which featured in 8 longest linear steps in with 13.9% total overall yield. The key synthetic strategy relied on the late-stage stille coupling for the macrolactonization to construct the 21-membered ring, while direct connection between the tripeptide fragment and the polyketide fragment failed. 1H NMR experiments reveal that nannocystin Ax should exist as conformational mixtures in deuterated solvents.

A motif-Oriented Total Synthesis of Nannocystin Ax. Preparation and Biological Assessment of Analogues

The highly cytotoxic cyclodepsipeptides of the nannocystin family are known to bind to the eukaryotic translation elongation factor 1α (EF-1α). Analysis of the docking pose, as proposed by a previous in silico study, suggested that the trisubstituted alkene moiety and the neighboring methyl ether form a domain that might be closely correlated with biological activity. This hypothesis sponsored a synthetic campaign which was designed to be motif-oriented : specifically, a sequence of ring closing alkyne metathesis (RCAM) followed by hydroxy-directed trans-hydrostannation of the resulting cycloalkyne was conceived, which allowed this potentially anchoring substructure to be systematically addressed at a late stage. This inherently flexible approach opened access to nannocystin Ax (1) itself as well as to 10 non-natural analogues. While the biological data confirmed the remarkable potency of this class of compounds and showed that the domain in question is indeed an innate part of the pharmacophore, the specific structure/activity relationships can only partly be reconciled with the original in silico docking study; therefore, we conclude that this model needs to be carefully revisited.

Total synthesis of nannocystin Ax

A concise total synthesis of nannocystin Ax, a natural depsipeptide recently isolated from myxobacteria, has been accomplished. By following a convergent strategy, the target molecule was assembled from three fragments. Each fragment can be synthesized expeditiously from readily achievable compounds. The key elements in this total synthesis feature Kobayashi's remote asymmetric induction with vinylketene silyl N,O-acetal, Roush's asymmetric crotylboration of aldehyde, Mitsunobu's esterification and macrocyclization via Stille cross-coupling.