137618-48-5

Basic information

• Product Name: BOC-(RS)-3-AMINO-1,2-PROPANEDIOL
• Synonyms: TERT-BUTYL N-(2,3-DIHYDROXYPROPYL)CARBAMATE;BOC-(RS)-3-AMINO-1,2-PROPANEDIOL;Carbamic acid, (2,3-dihydroxypropyl)-, 1,1-dimethylethyl ester (9CI);tert-Butyl (2,3-dihydroxypropyl)carbaMate;tert-Butyl N-(2,3-dihydroxypropyl)carbamate 97%;tert-Butyl (2,3-dihydroxypropyl);(2,3-dihydroxy-propyl)-carbamic acid tert-butyl ester
• CAS NO: 137618-48-5
• Molecular Formula: C₈H₁₇NO₄
• Molecular Weight: 191.22
• Product Categories: N-BOC;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 137618-48-5.mol

Chemical Properties

• Melting Point: 60-63 °C(lit.)
• Boiling Point: 361.6°C at 760 mmHg
• Flash Point: 172.5°C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 1.09E-06mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 12.19±0.46(Predicted)
• CAS DataBase Reference: BOC-(RS)-3-AMINO-1,2-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(RS)-3-AMINO-1,2-PROPANEDIOL(137618-48-5)
• EPA Substance Registry System: BOC-(RS)-3-AMINO-1,2-PROPANEDIOL(137618-48-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 137618-48-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
BOC-(RS)-3-AMINO-1,2-PROPANEDIOL is used as a protected amine intermediate for the synthesis of various pharmaceutical compounds. The protection of the amine group allows for selective functionalization at the hydroxyl groups, which can be crucial in the development of complex drug molecules.
Used in Chemical Research:
In the field of chemical research, BOC-(RS)-3-AMINO-1,2-PROPANEDIOL serves as a valuable building block for the creation of novel chemical entities. Its unique structure and reactivity make it an attractive candidate for the development of new materials and compounds with potential applications in various industries.
Used in Mass Spectrometric Analysis:
BOC-(RS)-3-AMINO-1,2-PROPANEDIOL is used in the preparation of isobaric mix solutions for post-column infusion experiments during single-stage orbitrap mass spectrometric analysis. The compound's unique properties make it suitable for use in this analytical technique, which is crucial for the identification and characterization of various biomolecules and chemical compounds.
Used in the Preparation of Glycerol Derivatives:
BOC-(RS)-3-AMINO-1,2-PROPANEDIOL can be used as a starting material for the synthesis of various glycerol derivatives. These derivatives find applications in a wide range of industries, including the pharmaceutical, cosmetic, and food industries, due to their diverse properties and functionalities.

InChI:InChI=1/C8H17NO4/c1-8(2,3)13-7(12)9-4-6(11)5-10/h6,10-11H,4-5H2,1-3H3,(H,9,12)

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 949086-94-6 tert-butyl[((+/-)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl]carbamate 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 137618-69-0 2-benzyloxy-3-((tert-butoxycarbonyl)amino)propanol 
• 137618-53-2 1-benzyloxy-3-((tert-butoxycarbonyl)amino)propan-2-ol 
• 195197-94-5 [3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]carbamic acid tert-butyl ester 
• 213475-72-0 3-((tert-butoxycarbonyl)amino)propane-1,2-diyl dimethanesulfonate 
• 89711-08-0 N-(t-butoxycarbonyl)glycinal 
• 1251455-27-2 tert-butyl N-(3-oxidanyl-2-oxidanylidenepropyl)carbamate 
• 1632462-24-8 C₅₃H₉₁NO₉ 
• 139200-36-5 methyl (2E)-4-{[(tert-butoxy)carbonyl]amino}but-2-enoate 

Relevant articles and documents

A Small Molecule That Switches a Ubiquitin Ligase from a Processive to a Distributive Enzymatic Mechanism

E3 ligases are genetically implicated in many human diseases, yet E3 enzyme mechanisms are not fully understood, and there is a strong need for pharmacological probes of E3s. We report the discovery that the HECT E3 Nedd4-1 is a processive enzyme and that disruption of its processivity by biochemical mutations or small molecules switches Nedd4-1 from a processive to a distributive mechanism of polyubiquitin chain synthesis. Furthermore, we discovered and structurally characterized the first covalent inhibitor of Nedd4-1, which switches Nedd4-1 from a processive to a distributive mechanism. To visualize the binding mode of the Nedd4-1 inhibitor, we used X-ray crystallography and solved the first structure of a Nedd4-1 family ligase bound to an inhibitor. Importantly, our study shows that processive Nedd4-1, but not the distributive Nedd4-1:inhibitor complex, is able to synthesize polyubiquitin chains on the substrate in the presence of the deubiquitinating enzyme USP8. Therefore, inhibition of E3 ligase processivity is a viable strategy to design E3 inhibitors. Our study provides fundamental insights into the HECT E3 mechanism and uncovers a novel class of HECT E3 inhibitors.

Interfacial cationization to quicken redox-responsive drug release

Interfacial cationization could greatly increase the redox-responsiveness of disulfide bond-linked lipid-drug nanoassemblies (NAs) due to the generation and concentration of ionized thiols at the alkalized NAs’ cationic interface. This strategy could be used to prepare redox-ultrasensitive nanocarriers for efficient intracellular drug delivery.

PH-Responsive Pharmacological Chaperones for Rescuing Mutant Glycosidases

A general approach is reported for the design of small-molecule competitive inhibitors of lysosomal glycosidases programmed to 1) promote correct folding of mutant enzymes at the endoplasmic reticulum, 2) facilitate trafficking, and 3) undergo dissociation and self-inactivation at the lysosome. The strategy is based on the incorporation of an orthoester segment into iminosugar conjugates to switch the nature of the aglycone moiety from hydrophobic to hydrophilic in the pH 7 to pH 5 window, which has a dramatic effect on the enzyme binding affinity. As a proof of concept, new highly pH-responsive glycomimetics targeting human glucocerebrosidase or α-galactosidase with strong potential as pharmacological chaperones for Gaucher or Fabry disease, respectively, were developed. pH-Responsive chaperones for rescuing mutant lysosomal glycosidases were developed by incorporating an acid-labile orthoester into sp2-iminosugar conjugates. In the endoplasmic reticulum (ER; pH 7), the chaperone binds to the mutant enzyme and promotes correct folding and trafficking. In the lysosome (pH 5), fast hydrolysis of the orthoester leads to inactivation of the chaperone.

5-hydroxypentane-2,3-dione and 3-amino-1-hydroxypropan-2-one, putative precursors of vitamin B6

New synthesis are described of 5-hydroxypentane-2,3-dione (7) (i.e., laurencione (7 ? 8)) and of 3-amino-1-hydroxypropan-2-one (3-amino-1- hydroxyacetone) (5) hydrochloride, putative precursors of the C5 unit, C- 2',2,3,4,4', and of the C3N unit, N-1,C-6,5,5', respectively, of pyridoxine (6). The condensation of hydroxypentane dione (i.e., laurencione) and aminohydroxypropanone forms a vitamin B, pyridoxine. The two compounds incorporated structural modifications on the formation mechanism of vitamin B. These compounds were considered as putative precursors of the C5 unit and the C3N unit of pyridoxine.

Orthoester functionalized: N -guanidino derivatives of 1,5-dideoxy-1,5-imino-d-xylitol as pH-responsive inhibitors of β-glucocerebrosidase

Alkylated guanidino derivatives of 1,5-dideoxy-1,5-imino-d-xylitol bearing an orthoester moiety were prepared using a concise synthetic protocol. Inhibition assays with a panel of glycosidases revealed that one of the compounds prepared displays potent inhibition against human β-glucocerebrosidase (GBA) at pH 7.0 with IC50 values in the low nanomolar range. Notably, a significant drop in inhibitory activity is observed when the same compound is tested at pH 5.2. This pH sensitive activity is due to degradation of the orthoester functionality at lower pH accompanied by loss of the alkyl group. This approach provides a degree of control in tuning enzyme inhibition based on the local pH. Compounds like those here described may serve as tools for studying various lysosomal storage disorders such as Gaucher disease. In this regard, the most active compound was also evaluated as a potential pharmacological chaperone by assessing its effect on GBA activity in an assay employing fibroblasts from Gaucher patients.

DIFLUOROHALOALLYLAMINE SULFONE DERIVATIVE INHIBITORS OF LYSYL OXIDASES, METHODS OF PREPARATION, AND USES THEREOF

The present invention relates to methods for preparing a variety of difluorohaloallylamine derivatives. The present invention also relates to novel difluorohaloallylamine derivatives that are capable of inhibiting certain amine oxidase enzymes. These compounds are useful for the treatment of a variety of indications, e.g., fibrosis, cancer and/or scarring in human subjects as well as in pets and livestock. In addition, the present invention relates to pharmaceutical compositions containing these compounds, as well as uses thereof.

Allylamine derivative as well as preparation method and application thereof

The invention relates to an allylamine derivative as well as a preparation method and application thereof, and in particular, relates to a compound represented by a formula I, or a stereoisomer, a tautomer, a polymorphic substance, a solvate, an N-oxide, an isotope labeled compound, a metabolite, a prodrug or ester thereof, or a pharmaceutically acceptable salt thereof. The compound has a higher inhibitory activity against vascular adhesion protein 1/semicarbazide sensitive amine oxidase, a good selectivity against monoamine oxidase and diamine oxidase; and additionally, in some embodiments, the mixture has a high in vivo bioavailability as well as safety.

Preparation and application of aminourea sensitive amine oxidase inhibitor

The invention provides preparation and application of an aminourea sensitive amine oxidase inhibitor. Specifically, the invention discloses a compound as shown in a formula I, or a stereoisomer, raceme or pharmaceutically acceptable salt thereof. The invention also discloses the compound capable of inhibiting the aminourea sensitive amine oxidase.

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.

Vinyl Sulfone-Based Inhibitors of Nonstructural Protein 2 Block the Replication of Venezuelan Equine Encephalitis Virus

Emerging infectious diseases like those caused by arboviruses such as Venezuelan equine encephalitis virus (VEEV) pose a serious threat to public health systems. Development of medical countermeasures against emerging infectious diseases are of utmost importance. In this work, an acrylate and vinyl sulfone-based chemical series was investigated as promising starting scaffolds against VEEV and as inhibitors of the cysteine protease domain of VEEV's nonstructural protein 2 (nsP2). Primary screen and dose response studies were performed to evaluate the potency and cytotoxicity of the compounds. The results provide structural insights into a new class of potent nonpeptidic covalent inhibitors of nsP2 cysteine protease represented by compound 11 (VEEV TrD, EC50= 2.4 μM (HeLa), 1.6 μM (Vero E6)). These results may facilitate the evolution of the compounds into selective and broad-spectrum anti-alphaviral drug leads.