(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate
CAS No.:1615251-38-1
Molecular Formula:C₃₄H₃₄INO₅
Molecular Weight:663.552
Hs Code.:

Synonyms:(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

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Chemical Property of (2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

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Technology Process of (2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

There total 5 articles about (2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate 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: 84.0%

: 1615251-34-7
(2S,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

: 1615251-38-1
(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; for 0.5h; Inert atmosphere; Reflux;
DOI:10.1039/c4ob00503a

Reference yield:

: benzyl (2R,3R,4R)-2,3-bis(benzyloxy)-4-hydroxy-1-(4-methoxyphenyl)-5-(trityloxy)pentylcarbamate

: 1615251-38-1
(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

4: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere; Reflux

With 1H-imidazole; dmap; potassium tert-butylate; iodine; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4ob00503a

Reference yield:

: benzyl (2R,3R,4R)-2,3-bis(benzyloxy)-4,5-dihydroxy-1-(4-methoxyphenyl)pentylcarbamate

: 1615251-38-1
(2R,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(iodomethyl)-5-(4-methoxyphenyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3: potassium tert-butylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

4: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

5: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere; Reflux

With 1H-imidazole; dmap; potassium tert-butylate; iodine; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4ob00503a