O-Benzyl-L-threonine hydrochloride
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O-Benzyl-L-threonine hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-006061
CAS number
60856-51-1
Molecular Formula
C11H16ClNO3
Molecular Weight
245.70
O-Benzyl-L-threonine hydrochloride
IUPAC Name
(2S,3R)-2-amino-3-phenylmethoxybutanoic acid;hydrochloride
Synonyms
H-Thr(Bzl)-OH HCl; (2S,3R)-2-Amino-3-benzyloxybutanoic acid hydrochloride
InChI
InChI=1S/C11H15NO3.ClH/c1-8(10(12)11(13)14)15-7-9-5-3-2-4-6-9;/h2-6,8,10H,7,12H2,1H3,(H,13,14);1H/t8-,10+;/m1./s1
InChI Key
XECHCUXLJZQHOJ-SCYNACPDSA-N
Canonical SMILES
CC(C(C(=O)O)N)OCC1=CC=CC=C1.Cl
1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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