(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

Base Information

Chemical Name:(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide
CAS No.:929896-09-3
Molecular Formula:C₂₅H₃₆IN₃O₆
Molecular Weight:601.482
Hs Code.:

Synonyms:(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

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Chemical Property of (2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

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Technology Process of (2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

There total 13 articles about (2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide 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: 75.0%

: 929896-15-1
(2R,3S)-1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-proline

: L-isoleucinamide acetic acid salt

: 929896-09-3
(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

Guidance literature:: With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;
DOI:10.1002/anie.200602865

Reference yield:

: 929896-10-6
(2R,3S)-1-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)methyl-3-(3-formyl-4-methoxy-phenoxy)-pyrrolidine

: 929896-09-3
(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / sodium hexamethyldisilazide; hexamethylphosphoramide; NaHCO₃ / tetrahydrofuran; H₂O / 2.33 h / -78 - 20 °C

2: 100 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0.83 h / -10 - 20 °C

3: 100 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 3.17 h / -78 - -10 °C

4: 486 mg / 2-methylprop-2-ene; sodium chlorite; sodium dihydrogen phosphate dihydrate / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 1 h

5: 75 percent / 1-hydroxybenzotriazole hydrate; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide / 16 h / 0 - 20 °C

With 4-methyl-morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Swern oxidation;
DOI:10.1002/anie.200602865

Reference yield:

: 929896-11-7
(2R,3S)-1-(tert-butoxycarbonyl)-2-(tert-butyldimethylsilyloxy)methyl-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-pyrrolidine

: 929896-09-3
(2R,3S)-{1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-prolyl}-isoleucinamide

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0.83 h / -10 - 20 °C

2: 100 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 3.17 h / -78 - -10 °C

3: 486 mg / 2-methylprop-2-ene; sodium chlorite; sodium dihydrogen phosphate dihydrate / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 1 h

4: 75 percent / 1-hydroxybenzotriazole hydrate; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide / 16 h / 0 - 20 °C

With 4-methyl-morpholine; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Swern oxidation;
DOI:10.1002/anie.200602865