102507-13-1

Basic information

• Product Name: N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
• Synonyms: (S)-N-ALPHA-T-BUTYLOXYCARBONYL-3,3-DIMETHYL-SERINE;(S)-2-BOC-AMINO-3-HYDROXY-3-METHYLBUTYRIC ACID;N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;BOC-S-SER(3,3ME2)-OH;BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID;BOC-L-SER(3,3-DIMETHYL);(S)-2-N-BOC-AMINO-3-HYDROXY-3-METHYLBUTYRIC ACID;(S)-Boc-beta,beta-dimethyl-serine
• CAS NO: 102507-13-1
• Molecular Formula: C₁₀H₁₉NO₅
• Molecular Weight: 233.26
• Product Categories: pharmacetical;unnatural amino acids
• Mol File: 102507-13-1.mol

Chemical Properties

• Melting Point: 116-118℃
• Boiling Point: 391.1 ºC at 760 mmHg
• Flash Point: 190.3 ºC
• Appearance: /
• Density: 1.175 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(102507-13-1)
• EPA Substance Registry System: N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID(102507-13-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 102507-13-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is used as a reagent for the synthesis of metabolites of PPI-2458, a selective, irreversible inhibitor of methionine aminopeptidase-2 (MetAP2). This application is significant in the development of potential therapeutic agents for various diseases.
Used in Hepatitis C Treatment:
N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is also used in the preparation of Boceprevir (B674500), an NS3 serine protease inhibitor of the hepatitis C virus. Boceprevir is an essential component in the treatment of HCV infection, helping to combat the virus and alleviate the symptoms associated with the disease.
Used in Research and Development:
In the field of research and development, N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID serves as a valuable compound for the synthesis of various pharmaceutical compounds and the study of their properties and potential applications in medicine.
Used in the Chemical Industry:
N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID is utilized in the chemical industry for the synthesis of various intermediates and specialty chemicals, contributing to the development of new products and technologies.

InChI:InChI=1/C10H19NO5/c1-9(2,3)16-8(14)11-6(7(12)13)10(4,5)15/h6,15H,1-5H3,(H,11,14)(H,12,13)/t6-/m1/s1

Upstream product

• 7758-19-2 sodium chlorite 
• 473545-40-3 tert-butyl N-[(1R)-2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]carbamate 
• 473452-22-1 methyl (S)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 182958-73-2 (2R)-2-(N-tert-Butoxycarbonyl)amino-3-hydroxy-3-methylbutanoic acid 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 1609644-37-2 C₂₀H₂₆N₂O₃ 
• 2280-27-5 (S)-2-amino-3-hydroxy-3-methylbutanoic acid 
• 34619-03-9 tert-butyldicarbonate 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 75-16-1 methylmagnesium bromide 
• 288159-36-4 tert-butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 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 
• 1275621-80-1 benzhydryl (S)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoate 
• 1422128-71-9 C₂₅H₃₀F₆N₄O₃S 
• 609367-41-1 3-hydroxy-N,N-dimethyl-L-valinamide 
• 123176-14-7 C₁₆H₃₆N⁽¹⁺⁾*C₁₀H₁₇N₂O₇S^(1-) 
• 102507-19-7 (S)-tert-butyl 1-(benzyloxyamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate 

Relevant articles and documents

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.

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.

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.

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.

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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.