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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

Quality Level

100

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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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