* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
[2-[4-(2-[<i>tert</i>-butoxycarbonyl-(2-thiophen-2-yl-ethyl)-amino]-methyl}-phenyl)-piperazin-1-yl]-1-(4-hydroxy-benzyl)-2-oxo-ethyl]-carbamic acid benzyl ester[ No CAS ]
{4-<i>tert</i>-butoxycarbonylmethyl-1-[2-(4-carbamimidoyl-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester[ No CAS ]
{4-<i>tert</i>-butoxycarbonylmethyl-1-[2-(4-carbamimidoyl-benzoylamino)-3-(4-hydroxy-phenyl)-propionyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester[ No CAS ]
(E)-(3S,6R,10R,16S)-3-Isobutyl-10-(4-methoxy-benzyl)-6-methyl-16-[(S)-1-((2S,3S)-3-phenyl-oxiranyl)-ethyl]-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone[ No CAS ]
Synthesis for the hin monomer class begins with stereochemicaily pure N-Cbz protected L-tyrosine 59 and uses the oxidative cyclization chemistry developed by Peter Wipf and co-workers[59] to form the bicyclic N-Cbz protected methyl-ester ketone 60.A Bucherer-Bergs reaction has been carried out on 60 and obtained two hydantoins 61 and 62 with a diastereomeric ratio of 3:1.These will be separated, their stereochemistry determined, and carried through to form two members of the hin monomer class.Several other stereoisomers of this class are accessible starting from D-tyrosine and through the extremely versatile chemistry developed by the Wipf group to alter the stereochemistry of the hydroindole core[59].
EXAMPLE 1 O-Benzyloxycarbonyl-D-tyrosine This compound was prepared from D-tyrosine (1.02 g) in the same manner as the L-isomer as described by Overell and Petrow, J. Chem. Soc. 232 (1955); yield, 0.73 g (40%); mp 208-210 decn; tlc (BAW) Ff 0.55; [alpha]D24 +9.1 (c 2.14, 80% acetic acid). Anal. Calcd for C17 H17 NO5 (315.325): C, 64.75; H, 5.43; N, 4.44. Found: C, 64.58; H, 5.48; N, 4.35.
methyl 3-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)propionate[ No CAS ]
[ 64205-12-5 ]
(R)-methyl 3-(4-(3-(2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanamido)phenyl)-1H-1,2,3-triazol-1-yl)propanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;
General procedure: To a stirred solution of the selected carboxylic acid (0.5 mmol) and HOBt (1.2 equiv/mol) in DMF, was added dropwise a solution of aniline 2 (0.5 mmol.) in DMF. EDC (1.2 equiv/mol) was then added portionwise and the mixture was stirred overnight at rt.The crude reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3 15 mL). The combined organic layers were washed with brine (3 15 mL), dried over anhydrous MgSO4,filtered and concentrated under reduced pressure to give a residue, which was purified as indicated for each compound in the Supporting material.