(S)-1-Boc-3-hydroxypiperidine - CAS 143900-44-1
Catalog number: 143900-44-1
Category: Inhibitor
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Molecular Formula:
C10H19NO3
Molecular Weight:
201.26
COA:
Inquire
Targets:
Others
Description:
This molecular is a piperidine derivative with an amine protecting group. It may be used in the preparation of biologically active compounds like selective irreversible inhibitors for brutons tyrosine kinase and antagonists of the human P2X7 receptor.
Purity:
98%
Appearance:
White to Pale Yellow Low Melting Solid
Synonyms:
(3S)-3-Hydroxy-1-piperidinecarboxylic Acid 1,1-dimethylethyl Ester; (S)-3-Hydroxypiperidine-1-carboxylic Acid tert-Butyl Ester; (S)-N-Boc-3-hydroxypiperidine; (S)-tert-Butyl 3-Hydroxypiperidine-1-carboxylate; 1,1-Dimethylethyl (3S)-3-Hydroxy-1-piperidinecarboxylate; 1-Boc-(3S)-3-hydroxypiperidine; tert-Butyl (S)-3-Hydroxypiperidine-1-carboxylate; (S)-N-Boc-3-hydroxypiperidine;
Solubility:
Chloroform, Ethyl Acetate
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
preparation of biologically active compounds like selective irreversible inhibitors for brutons tyrosine kinase and antagonists of the human P2X7 receptor.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Boiling Point:
No Data Available
Melting Point:
46-49°C
InChIKey:
UIJXHKXIOCDSEB-QMMMGPOBSA-N
InChI:
InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-5-8(12)7-11/h8,12H,4-7H2,1-3H3/t8-/m0/s1
Canonical SMILES:
CC(C)(C)OC(=O)N1CCCC(C1)O
1.Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: enantioselective synthesis of polyhydroxypiperidines.
Amat M;Llor N;Huguet M;Molins E;Espinosa E;Bosch J Org Lett. 2001 Oct 18;3(21):3257-60.
[reaction: see text]. The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxypiperidine is also reported.
2.Efficient synthesis of (S)-N-Boc-3-hydroxypiperidine using an (R)-specific carbonyl reductase from Candida parapsilosis.
Chen J;Yan M;Xu L World J Microbiol Biotechnol. 2017 Mar;33(3):61. doi: 10.1007/s11274-016-2189-y. Epub 2017 Feb 27.
(S)-N-Boc-3-hydroxypiperidine (S-NBHP) is a critical chiral intermediate in the synthesis of pharmaceuticals, including ibrutinib, the active pharmaceutical ingredient of the new drug Imbruvica approved for the treatment of lymphoma. An (R)-specific carbonyl reductase from Candida parapsilosis (CprCR, also known as R-specific alcohol dehydrogenase) that catalyzes asymmetric reduction to produce (S)-N-Boc-3-hydroxypiperidine (S-NBHP) was identified for the first time. When co-expressed with a glucose dehydrogenase from Bacillus megaterium in Escherichia coli Rosetta (DE3), recombinant crude enzyme exhibited an activity of 9 U/mg with N-Boc-3-piperidone as the substrate and 12 U/mg with glucose as the substrate. The biocatalysis of N-Boc-3-piperidone to S-NBHP using recombinant whole-cell biocatalysts was processed in a water/butyl acetate system as well as an aqueous monophasic system without extra NAD;+;/NADH. This process showed great commercial potential, with a 100 g/l substrate concentration and a whole cells loading (w/v) of 10%, with the conversion of 97.8% and an e.e. of 99.8% in an aqueous monophasic system.
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CAS 143900-44-1 (S)-1-Boc-3-hydroxypiperidine

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