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

Base Information

Chemical Name:(2R,3S)-1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-proline
CAS No.:929896-15-1
Molecular Formula:C₁₉H₂₄INO₆
Molecular Weight:489.307
Hs Code.:

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

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

Chemical Property:

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

There total 12 articles about (2R,3S)-1-(tert-butoxycarbonyl)-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-proline 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:

: 929896-14-0
(2R,3S)-1-(tert-butoxycarbonyl)-2-formyl-3-[3-((Z)-2-iodovinyl)-4-methoxy-phenoxy]-pyrrolidine

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

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol; for 1h;
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

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

Guidance literature:: Multi-step reaction with 4 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

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 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

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

Guidance literature:: Multi-step reaction with 3 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

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2: Swern oxidation;
DOI:10.1002/anie.200602865