Benzyl-O-tert-butyl-L-serine methyl ester hydrochloride
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Benzyl-O-tert-butyl-L-serine methyl ester hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-003901
CAS number
670278-82-7
Molecular Formula
C15H23NO3·HCl
Molecular Weight
301.84
Benzyl-O-tert-butyl-L-serine methyl ester hydrochloride
IUPAC Name
methyl (2S)-2-(benzylamino)-3-[(2-methylpropan-2-yl)oxy]propanoate;hydrochloride
Synonyms
Bzl-L-Ser(tBu)-OMe HCl; (S)-Methyl 2-(benzylamino)-3-(tert-butoxy)propanoate hydrochloride; N-BENZYL-O-T-BUTYL-L-SERINE METHYL ESTER HYDROCHLORIDE
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Melting Point
133-139 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C15H23NO3.ClH/c1-15(2,3)19-11-13(14(17)18-4)16-10-12-8-6-5-7-9-12;/h5-9,13,16H,10-11H2,1-4H3;1H/t13-;/m0./s1
InChI Key
ANYVZGGUHIDNDZ-ZOWNYOTGSA-N
Canonical SMILES
CC(C)(C)OCC(C(=O)OC)NCC1=CC=CC=C1.Cl
1. l-Serine methyl ester hydro-chloride
Arie Schouten, Martin Lutz Acta Crystallogr Sect E Struct Rep Online. 2009 Nov 7;65(Pt 12):o3026. doi: 10.1107/S1600536809046480.
In the enanti-opure crystal of the title compound, C(4)H(10)NO(3) (+)·Cl(-), inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds link the mol-ecules into layers parallel to (001).
2. 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.
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