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706531

Sigma-Aldrich

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

95%

Synonym(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

Empirical Formula (Hill Notation):
C16H28BNO4
CAS Number:
286961-14-6
Molecular Weight:
309.21
MDL number:
MFCD03840345
UNSPSC Code:
12352103
PubChem Substance ID:
329762650
NACRES:
NA.22

Assay

95%

form

powder

mp

100-114 °C

SMILES string

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

InChI key

VVDCRJGWILREQH-UHFFFAOYSA-N

Related Categories

General description

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperidin-3-yl-cyclopropanecarboxamide derivatives as novel melatonin receptor ligands
Li, G.; et al.
Bioorganic & Medicinal Chemistry, 21, 1236-1242 (2011)
Paul M Wehn et al.
Organic letters, 11(24), 5666-5669 (2009-12-17)
A novel approach to the synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles beginning from a common precursor has been achieved. Derivatization by palladium-catalyzed Suzuki-Miyaura coupling enables the rapid preparation of analogs around this pharmaceutically relevant core. FMO calculations rationalize the observed
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.
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
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)
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