(R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

Base Information

Chemical Name:(R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid
CAS No.:1393723-93-7
Molecular Formula:C₂₉H₃₃N₃O₉
Molecular Weight:567.596
Hs Code.:

Synonyms:

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Chemical Property of (R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

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Technology Process of (R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

There total 3 articles about (R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: H-β-Ala-2-ClTrt resin

: 1393723-62-0
NVOC-p-I-D-Phe-OH

: 14272-54-9,14272-82-3,65050-58-0
(E)-3-ethyl-pent-3-en-1-yne

: 1393723-93-7
(R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

Guidance literature:: H-β-Ala-2-ClTrt resin; NVOC-p-I-D-Phe-OH; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; solid phase reaction;

(E)-3-ethyl-pent-3-en-1-yne; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In 1,4-dioxane; at 25 ℃; Inert atmosphere; Darkness; solid phase reaction;

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 1h; solid phase reaction;
DOI:10.1002/chem.201200952

Reference yield:

: 42855-00-5
nitroveratryloxycarbonyl chloride

: 1393723-93-7
(R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 25 °C

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / solid phase reaction

2.2: 25 °C / Inert atmosphere; Darkness; solid phase reaction

2.3: 1 h / 25 °C / solid phase reaction

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 2.2: Sonogashira reaction;
DOI:10.1002/chem.201200952

Reference yield:

: 62561-75-5
(R)-2-amino-3-(4-iodophenyl)propanoic acid

: 1393723-93-7
(R,E)-3-(2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(4-(3-ethylpent-3-en-1-ynyl)phenyl)propanamido)propanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 25 °C

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C / solid phase reaction

2.2: 25 °C / Inert atmosphere; Darkness; solid phase reaction

2.3: 1 h / 25 °C / solid phase reaction

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 2.2: Sonogashira reaction;
DOI:10.1002/chem.201200952