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706531

Sigma-Aldrich

N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester

95%

Synonyme(s) :

(1-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester, (N-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester, (N-tert-Butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)boronic acid pinacol ester, (N-tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester

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About This Item

Formule empirique (notation de Hill):
C16H28BNO4
Numéro CAS:
286961-14-6
Poids moléculaire :
309.21
Numéro MDL:
MFCD03840345
Code UNSPSC :
12352103
ID de substance PubChem :
329762650
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

95%

Forme

powder

Pf

100-114 °C

Chaîne SMILES 

CC(C)(C)OC(=O)N1CCC(=CC1)B2OC(C)(C)C(C)(C)O2

InChI

1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3

Clé InChI

VVDCRJGWILREQH-UHFFFAOYSA-N

Catégories apparentées

Description générale

Boc-THP-Bpin is frequently used in metal catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Negishi couplings.

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling using palladium phosphine catalyst
  • Palladium-catalyzed ligand-controlled regioselective Suzuki coupling
  • Palladium-catalyzed Suzuki-Miyaura coupling
  • Suzuki coupling followed by iodolactonization reaction
  • Wrenchnolol derivative optimized for gene activation in cells

Reagent used in Preparation of several enzymatic inhibitors and receptor ligands
  • Orally active anaplastic lymphoma kinase inhibitors
  • Oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes
  • 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides as novel melatonin receptor ligands
  • Quinazoline analogs as glucocerebrosidase inhibitors with chaperone activity for treatment of Gaucher disease, a lysosomal storage disorder
  • Arylpiperazine and piperidine ethers as dual acting norepinephrine reuptake inhibitors and 5-HT1A partial agonists

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Sigma-Aldrich

216666

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Discovery and pharmacological characterization of aryl piperazine and piperidine ethers as dual acting norepinephrine reuptake inhibitors and 5-HT1A partial agonists
Gray, D. L.; et al.
Bioorganic & Medicinal Chemistry, 19, 6604-6607 (2009)
Yimin Qian et al.
Journal of medicinal chemistry, 54(7), 2433-2446 (2011-03-19)
Diacylglycerol acyltransferase-1 (DGAT-1) is the enzyme that catalyzes the final and committed step of triglyceride formation, namely, the acylation of diacylglycerol with acyl coenzyme A. DGAT-1 deficient mice demonstrate resistance to weight gain on high fat diet, improved insulin sensitivity
Preparation of 3,4-fused-spiro[furan-5(5H),4'-piperidin]-2-one
Liu, J.; et al.
Tetrahedron Letters, 50, 5228-5230 (2009)
Kazutomo Kinoshita et al.
Bioorganic & medicinal chemistry, 20(3), 1271-1280 (2012-01-10)
Anaplastic lymphoma kinase (ALK) receptor tyrosine kinase is considered an attractive therapeutic target for human cancers, especially non-small cell lung cancer (NSCLC). Our previous study revealed that 8,9-side-chains of 6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole scaffold crucially affected kinase selectivity, cellular activity, and metabolic stability.
Juan J Marugan et al.
Journal of medicinal chemistry, 54(4), 1033-1058 (2011-01-22)
Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described
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