S-Trityl-D-cysteine methyl ester hydrochloride
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S-Trityl-D-cysteine methyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-001583
CAS number
1020369-32-7
Molecular Formula
C23H24ClNO2S
Molecular Weight
413.97
IUPAC Name
methyl (2S)-2-amino-3-tritylsulfanylpropanoate;hydrochloride
Synonyms
H-D-Cys(Trt)-OMe HCl
InChI
InChI=1S/C23H23NO2S.ClH/c1-26-22(25)21(24)17-27-23(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20;/h2-16,21H,17,24H2,1H3;1H/t21-;/m1./s1
InChI Key
BBLIVDURNAQWLB-ZMBIFBSDSA-N
Canonical SMILES
COC(=O)C(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)N.Cl
2. An efficient enantioselective synthesis of ( S)-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination
Qiong Xiao, Yi-Fan Tang, Ping Xie J Asian Nat Prod Res. 2020 Jan;22(1):61-68. doi: 10.1080/10286020.2019.1634058. Epub 2019 Jul 16.
We present the synthesis of enantiomerically pure (S)-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di-p-chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine derivative catalyst. The application of the organocatalyst of D-3-(1-Naphthyl)-alanine is the key step in the synthesis and ensures the product is obtained with high levels of stereocontrol.
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