O-Benzyl-L-trans-4-hydroxyproline methyl ester hydrochloride
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O-Benzyl-L-trans-4-hydroxyproline methyl ester hydrochloride

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Category
Cyclic Amino Acids
Catalog number
BAT-005708
CAS number
66831-17-2
Molecular Formula
C13H17NO3·HCl
Molecular Weight
271.75
O-Benzyl-L-trans-4-hydroxyproline methyl ester hydrochloride
IUPAC Name
methyl (2S,4R)-4-phenylmethoxypyrrolidine-2-carboxylate;hydrochloride
Synonyms
L-Hyp(Bzl)-OMe HCl
Appearance
Off-white powder
Purity
≥ 98% (NMR)
Storage
Store at 2-8°C
InChI
InChI=1S/C13H17NO3.ClH/c1-16-13(15)12-7-11(8-14-12)17-9-10-5-3-2-4-6-10;/h2-6,11-12,14H,7-9H2,1H3;1H/t11-,12+;/m1./s1
InChI Key
DTGIEBXEDOSJQH-LYCTWNKOSA-N
Canonical SMILES
COC(=O)C1CC(CN1)OCC2=CC=CC=C2.Cl
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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