128427-10-1

Basic information

• Product Name: (S)-(-)-2-(Boc-Amino)-1,4-butanediol
• Synonyms: (S)-(-)-N-Boc-2-Amino-1,4-butanediol;Carbamic acid, [(1S)-3-hydroxy-1-(hydroxymethyl)propyl]-, 1,1-dimethylethyl;(S)-(-)-2-(boc-Amino)-1,4-butendiol;(S)-N-BOC-2-AMINO-BUTANE-1,4-DIOL ;(S)-TERT-BUTYL 1,4-DIHYDROXYBUTAN-2-YLCARBAMATE;(S)-N-BOC-2-AMINO-BUTANE-1,4-DIOL ,97%;(S)-(-)-2-(Boc-Amino)-1,4-butanediol;(S)-(3-Hydroxy-1-hydroxymethylpropyl)carbamic acid tert-butyl ester
• CAS NO: 128427-10-1
• Molecular Formula: C₉H₁₉NO₄
• Molecular Weight: 205.25
• Product Categories: N-BOC;API intermediates;Amino Alcohols;Chiral Building Blocks;Organic Building Blocks;Chiral Compounds
• Mol File: 128427-10-1.mol

Chemical Properties

• Melting Point: 65-69 °C(lit.)
• Boiling Point: 365 °C at 760 mmHg
• Flash Point: 174.6 °C
• Appearance: White/Crystalline Powder
• Density: 1.11 g/cm³
• Vapor Pressure: 8.28E-07mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• PKA: 11.81±0.46(Predicted)
• CAS DataBase Reference: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(128427-10-1)
• EPA Substance Registry System: (S)-(-)-2-(Boc-Amino)-1,4-butanediol(128427-10-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 128427-10-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-2-(Boc-Amino)-1,4-butanediol is used as a reactant for the synthesis of various organic compounds, particularly in the development of novel catalysts for asymmetric reactions. Its unique structure allows for the creation of chiral catalysts that can improve the selectivity and efficiency of chemical processes.
Used in Pharmaceutical Industry:
(S)-(-)-2-(Boc-Amino)-1,4-butanediol is used as a building block for the synthesis of chiral pharmaceuticals. Its Boc-protected amino group and hydroxyl groups can be utilized in the development of new drugs with improved pharmacological properties and reduced side effects.
Used in Catalyst Development:
(S)-(-)-2-(Boc-Amino)-1,4-butanediol is used as a reactant to synthesize thiourea-based organocatalysts for asymmetric Michael addition reactions of nitroalkenes to α-nitrocyclohexanone. These catalysts play a crucial role in the synthesis of complex organic molecules with high enantioselectivity, which is essential for the development of chiral drugs and other biologically active compounds.
Used in Enantioselective Catalysis:
(S)-(-)-2-(Boc-Amino)-1,4-butanediol is also used in the synthesis of bis-copper (II) complex-based catalysts for enantioselective Michael reactions. These catalysts are important in the production of optically active compounds, which are often required for the biological activity of pharmaceuticals and agrochemicals.

InChI:InChI=1/C9H19NO4/c1-9(2,3)14-8(13)10-7(6-12)4-5-11/h7,11-12H,4-6H2,1-3H3,(H,10,13)/t7-/m0/s1

Upstream product

• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 146514-35-4 (RS)-N-tert-butoxycarbonyl-α-amino-γ-butyrolactone 
• 56-84-8 L-Aspartic acid 
• 128427-09-8 (S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester 
• 10405-07-9 (2S)-2-amino-1,4-butanediol 
• 13726-67-5 Boc-Asp-OH 

Downstream Products

• 850996-84-8 (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-triisopropylsilanyloxypentanoic acid 
• 850996-94-0 (4S)-[(2S)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 850996-90-6 (4S)-[(2R)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 329912-53-0 (3S,5R)-[5-(benzyloxycarbonylaminomethyl)-2-oxotetrahydrofuran-3-yl]carbamic acid tert-butyl ester 
• 122536-76-9 3(S)-(tert-butoxycarbonylamino)pyrrolidine 
• 131852-53-4 (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine 
• 186366-83-6 2-{2-[5-((S)-3-tert-Butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-pentyl]-benzyl}-malonic acid monomethyl ester 
• 852874-60-3 (S)-tert-butyl 1-methylpyrrolidin-3-ylcarbamate 
• 1619261-23-2 (S)-tert-butyl-(2-(2-tosyloxy)ethyl)aziridine-1-carboxylate 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 104227-71-6 N-[(3S)-tetrahydro-5-oxo-3-furanyl]carbamic acid-1,1-dimethylethyl ester 
• 205491-16-3 (S)-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate 

Relevant articles and documents

JM-PHOS ligands: Second-generation phosphine oxazolines for asymmetric catalysis

(formula presented) A small library of phosphine oxazollne ligands 2 was prepared and tested in palladium-mediated allylation processes (reactions 1 and 2). They were found to be superior to the first-generation ligands 1 and as effective as the well-know

Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation

A convenient approach towards the synthesis of orthogonally protected chiral bis-a-amino acids (OPBAAs) is described. The key transformations include: (1) a highly stereoselective conjugation (alkylation) of the Sch?llkopf bislactim ethers and oxazolidinyl alkyl halides to build a backbone skeleton; and (2) our orthogonal protection strategy. A series of enantiopure OPBAAs bearing a variety of alkyl chain as a spacer; two stereogenic centers; and three protecting groups were prepared as examples. These versatile molecules were applied to the synthesis of biologically interesting di- or tri-peptide analogues, including chiral iE-meso-DAP and A-iE-meso-DAP, for the study of Nod1 activation in the innate immune response.

β-Hydroxy- A nd β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth

Malaria is an infectious disease caused by a parasite of the genus Plasmodium, and the emergence of parasites resistant to all current antimalarial drugs highlights the urgency of having new classes of molecules. We developed an effective method for the synthesis of a series of β-modified acyclonucleoside phosphonate (ANP) derivatives, using commercially available and inexpensive materials (i.e., aspartic acid and purine heterocycles). Their biological evaluation in cell culture experiments and SAR revealed that the compounds' effectiveness depends on the presence of a hydroxyl group, the chain length (four carbons), and the nature of the nucleobase (guanine). The most active derivative inhibits the growth of Plasmodium falcIParum in vitro in the nanomolar range (IC50 = 74 nM) with high selectivity index (SI > 1350). This compound also showed remarkable in vivo activity in P. berghei-infected mice (ED50 ～0.5 mg/kg) when administered by the IP route and is, although less efficient, still active via the oral route. It is the first ANP derivative with such potent antimalarial activity and therefore has considerable potential for development as a new antimalarial drug.

A stereocontrolled synthetic route to anti-β-amino alcohols

A physiologically indispensable β-amino hydroxy functionality has been constructed with complete anti-stereoselectivity by intramolecular iodoamidation of (Z)-olefinic homoallylic trichloroacetimidates 4-6, 18, 20, 30 and 32, which comprise bulky substituents at the vinylic positions.

Design and synthesis of a novel site-directed reducing agent for the disulfide bond involved in the acetylcholine binding site of the AChoR

The 2-trimethylammonioethyloxycarbonylamino-1,4-butanedithiol 7 was synthesized and tested as a site-directed reducing agent for the disulfide bond involved in the acetylcholine binding site of the AChoR, which was then specifically labeled by an undecagold cluster.

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.

Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism

A broad range of N-carbamoylaziridines were obtained and then treated by the diethyl phosphonate anion to afford α-methylene-gem-bisphosphonate aziridines. Study of the reaction's scope and additional experiments indicates that the transformation proceeds via a new mechanism involving the chelation of lithium ion. This last step is crucial for the reaction to occur and disfavors the aziridine ring-opening. A phosphonate-phosphate rearrangement from a α-hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides a simple and convenient method for the synthesis of a highly functionalized phosphonylated aziridine motif.

Enantioselective Hydrogenation of Racemic α-Arylamino Lactones to Chiral Amino Diols with Site-Specifically Modified Chiral Spiro Iridium Catalysts

A protocol for highly enantioselective hydrogenation of racemic α-arylamino lactones with catalysis by site-specifically modified chiral spiro iridium complexes has been developed. With the optimized catalyst, racemic α-arylamino-γ-lactones and α-arylamino-δ-lactones could be hydrogenated to the corresponding chiral 2-amino diols with good to excellent enantioselectivities.

DITHIOAMINE REDUCING AGENTS

Dithioamine reducing agents useful for the reduction of disulfide bonds. The reducing agents of this invention are useful, for example, to reduce disulfide bonds, particularly in proteins, or to prevent the formation of disulfide bonds, particularly in proteins and other biological molecules. Reducing agents of this invention are useful and suitable for application in a variety of biological applications, particularly as research and synthetic reagents. The invention provides S-acylated dithioamines which can be selectively activated reducing agents by removal of the S-acyl groups enzymatically or chemically. The invention further provides dithiane precursors of thioamino reducing agents. The invention provides dithioamine reducing agents, S-acylated dithioamines and dithianes which are immobilized on surfaces, including among others, glass, quartz, microparticles, nanoparticles and resins.

DITHIOAMINE REDUCING AGENTS

Dithioamine reducing agents useful for the reduction of disulfide bonds. The reducing agents of this invention are useful, for example, to reduce disulfide bonds, particularly in proteins, or to prevent the formation of disulfide bonds, particularly in proteins and other biological molecules. Reducing agents of this invention can be employed to regulate protein function in proteins in which a sulfhydryl group is associated with biological activity. Reducing agents of this invention can prevent inactivation of a given protein or enhance activation of a given protein or other biological molecule in vitro and/or in vivo. Reducing agents of this invention can prevent or reduce oxidation of cysteine residues in proteins and prevent the formation of reduced activity protein dimers (or other oligomers). Reducing agents of this invention are useful and suitable for application in a variety of biological applications, particularly as research and synthetic reagents.