β-Cyclohexyl-D-alanine methyl ester hydrochloride
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β-Cyclohexyl-D-alanine methyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-005818
CAS number
144644-00-8
Molecular Formula
C10H19NO2·HCl
Molecular Weight
221.70
β-Cyclohexyl-D-alanine methyl ester hydrochloride
IUPAC Name
methyl (2R)-2-amino-3-cyclohexylpropanoate;hydrochloride
Synonyms
D-Cha-OMe HCl; 3-Cyclohexyl-D-alanine methyl ester hydrochloride
Appearance
White powder
Purity
≥ 99% (Chiral purity)
Storage
Store at 2-8°C
InChI
InChI=1S/C10H19NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h8-9H,2-7,11H2,1H3;1H/t9-;/m1./s1
InChI Key
YLESODBCBYZUCT-SBSPUUFOSA-N
Canonical SMILES
COC(=O)C(CC1CCCCC1)N.Cl
1. Asymmetric Total Synthesis of Griseofamine B and Its Three Stereoisomers
Tao Sheng, Caiyun Ma, Guangyan Zhang, Xuan Pan, Zhanzhu Liu J Nat Prod. 2022 Apr 22;85(4):1128-1133. doi: 10.1021/acs.jnatprod.2c00069. Epub 2022 Mar 3.
The first total synthesis of griseofamine B is described starting from l-4-bromo tryptophan methyl ester hydrochloride via five steps and in 18% overall yield. Its three stereoisomers were also synthesized following the same procedure with the yields of 5%, 19%, and 5%, respectively. In vitro antibacterial activities were also evaluated. All four compounds exhibited less potent activity than griseofamine A.
2. l-Alanine methyl ester hydro-chloride monohydrate
Martin Lutz, Arie Schouten Acta Crystallogr Sect E Struct Rep Online. 2011 Feb 9;67(Pt 3):o586. doi: 10.1107/S160053681100420X.
The enanti-opure title compound, C(4)H(10)NO(2) (+)·Cl(-)·H(2)O, forms a two-dimensional network by inter-molecular hydrogen bonding parallel to (010). Non-merohedral twinning with a twofold rotation about the reciprocal c* axis as twin operation was taken into account during intensity integration and structure refinement. This twinning leads to alternative orientations of the stacked hydrogen-bonded layers.
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