397246-12-7

Basic information

• Product Name: (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL
• Synonyms: BOC-R-GLU-OL2;(R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL;Carbamic acid, [(1R)-4-hydroxy-1-(hydroxymethyl)butyl]-, 1,1-dimethylethyl
• CAS NO: 397246-12-7
• Molecular Formula: C10H21NO4
• Molecular Weight: 219.28
• Product Categories: N-BOC
• Mol File: 397246-12-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL(397246-12-7)
• EPA Substance Registry System: (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL(397246-12-7)

Safety Data

• Hazardous Substances Data: 397246-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL is used as a building block for the synthesis of various pharmaceuticals, given its role in creating peptides and peptidomimetics. (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL contributes to the development of new drugs by providing a stable and easily synthesized foundation for medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL serves as a crucial component for creating complex organic molecules. Its protective Fmoc group allows for selective reactions, making it a valuable asset in the synthesis of a wide range of organic compounds.
Used in Peptide Chemistry:
(R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL is used as a building block for the synthesis of peptides. (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL's protected form of L-lysine enables the formation of peptide bonds in a controlled manner, which is essential for the development of peptide-based therapeutics and other applications.
Used in Solid-Phase Peptide Synthesis:
As a reagent in solid-phase peptide synthesis, (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL is utilized for its stability and ease of synthesis. This method of peptide synthesis is highly valued for its efficiency and the ability to create large quantities of peptides with minimal side reactions, thanks in part to the use of (R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL.
Used in the Synthesis of Natural Products:
(R)-2-TERT-BUTYLOXYCARBONYLAMINO-PENTANE-1,5-DIOL is also used in the preparation of various natural products. Its role in peptide and organic synthesis makes it a versatile tool for creating complex natural compounds with potential applications in the fields of medicine, agriculture, and other industries.

Upstream product

• 4931-66-2 methyl (S)-pyroglutamate 
• 861658-15-3 1,5-dimethyl (2R)-2-[[(tert-butoxy)carbonyl]amino]pentanedioate 
• 478646-28-5 (R)-2-Cbz-aminopentan-1,5-diol 
• 861658-15-3 1,5-dimethyl 2-[(t-butoxycarbonyl)amino]pentanedioate 
• 617-65-2 Glutamic acid 
• 6525-53-7 glutamic acid dimethyl ether 
• 34404-28-9 N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 16422-27-8 1,5-dimethyl (2R)-2-aminopentanedioate 
• 6893-26-1 D-Glutamic acid 
• 56-86-0 L-glutamic acid 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 125982-23-2 ⁽⁵⁾-tert-butyl (6-oxotetrahydro-2H-pyran-3-yl)carbamate 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 
• 454713-13-4 tert-butyl (R)-(+)-(N-benzylpiperidin-3-yl)carbamate 
• 478828-62-5 (1-benzylpiperidin-3-yl)carbamic acid tert-butyl ester 
• 121706-11-4 (-)-n-Hexyl indolactam V 
• 1607592-28-8 [(5S)-5-aminotetrahydro-2H-pyran-2-yl]acetonitrile hydrochloride 
• 71974-09-9 γ-D-Glutamyl-L-meso-diaminopimelic acid dipeptide 
• 1295568-51-2 (S)-N-(tetrahydro-2H-pyran-3-yl)cinnamamide 
• 1295722-66-5 (S)-tert-butyl (tetrahydro-2H-pyran-3-yl)carbamate 
• 1157849-50-7 C₆H₁₄N₂*(x)ClH 
• 84590-48-7 indolactam V 

Relevant articles and documents

Synthetic process of anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride

The invention relates to a synthetic process of an anti-hyperglycemic drug intermediate R-3-amino-piperidine dihydrochloride. The synthetic process comprises the steps: using inexpensive L-glutamic acid as a starting material, and performing esterification, amino protection, reduction, hydroxyl protection, substitution, cyclization and removal of protecting groups for amino groups so as to obtainthe R-3-amino-piperidine dihydrochloride. Compared with the prior art, the synthetic process has cheap and easily available raw materials, good selectivity, good atomic economy, high total yield and mild reaction conditions, and is suitable for industrial production.

Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells

Human proteinase-activated receptor 2 (PAR2), a transmembrane G-protein-coupled receptor (GPCR), is an attractive target for a novel anticancer therapy, as it plays a critical role in cell migration and invasion. Selective PAR2 inhibitors therefore have potential as anti-metastatic drugs. Knowing that the natural product teleocidin A2 is able to inhibit PAR2 in tumor cells, the goal of the present study was to elaborate structure–activity relationships and to identify potent PAR2 inhibitors with lower activity against the adverse target, protein kinase C (PKC). For this purpose, an efficient gram-scale total synthesis of indolactam V (i.e., the parent structure of all teleocidins) was developed, and a library of derivatives was prepared. Some compounds were indeed found to exhibit high potency as PAR2 inhibitors at low nanomolar concentrations with improved selectivity (relative to teleocidin A2). The pseudopeptidic fragment bridging the C3 and C4 positions of the indole core proved to be essential for target binding, whereas activity and target selectivity depends on the substituents at N1 or C7. This study revealed novel derivatives that show high efficacy in PAR2 antagonism combined with increased selectivity.

CALPAIN MODULATORS AND METHODS OF PRODUCTION AND USE THEREOF

The present technology relates to compounds, kits, compositions, and methods useful for the treatment of fibrotic disease. In some aspects, the present technology provides for treatment of various diseases or disorders associated or mediated, at least in part, by calpains, such as CAPN1, CAPN2, and/or CAPN9. The present technology is generally applicable to compounds which inhibit myofibroblast differentiation.

(R) - 3-amino-piperidine dihydrochloride preparation method

The invention discloses a method for preparing (R)-3-amino piperidine hydrochloride. D-glutamic acid is taken as a starting material, and the (R)-3-amino piperidine hydrochloride is obtained by reaction in the following five steps: (1) hydroxyl esterification and amido Boc protection; (2) ester reduction; (3) hydroxyl activation; (4) cyclization; (5) amino Boc removal protection. The preparation method disclosed by the invention is short in synthetic route and low in cost, and industrial production can be achieved.

Amino-protected (R) - 3-amino-piperidine preparation method

The invention discloses a preparation method of amino protection (R)-3-amino piperidine, and the preparation method comprises the following steps: (1) in the presence of a first solvent or absence of a solvent, reacting a compound of formula V with benzylamine to obtain a compound of formula VI; (2) in the presence of a second solvent, performing catalytic hydrogenation of the compound of formula VI to remove benzyl to obtain the amino protection (R)-3-amino piperidine. According to the method, the defects of use of expensive metal catalysts and use of high-pressure hydrogenation and various splitting for synthesis of a chiral amino piperidine ring can be avoided, at the same time, the synthetic route is short, the process is simple, the yield is high, and the method is suitable for industrial mass production.

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

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PROCESSES OF PREPARING A JAK1 INHIBITOR AND NEW FORMS THERETO

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TRICYCLIC HETEROCYCLIC COMPOUNDS, COMPOSITIONS AND METHODS OF USE THEREOF AS JAK INHIBITORS

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Kilogram synthesis of (S)-3-aminopyran from l -glutamic acid

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