(2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 1615251-25-6
• Molecular Formula: C₅₉H₅₃NO₆
• Molecular Weight: 872.073

Synonyms:(2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate

Chemical Property of (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate

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Technology Process of (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate

There total 2 articles about (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)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:

C60H57NO9S → (2S,3R,4R,5S)-benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate (1615251-24-5) + (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate (1615251-25-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4ob00503a

Reference yield:

benzyl (2R,3R,4R)-2,3-bis(benzyloxy)-1-(4-(benzyloxy)-phenyl)-4,5-dihydroxypentylcarbamate → (2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate (1615251-25-6)

Guidance literature:

Multi-step reaction with 3 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

With dmap; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c4ob00503a

Reference yield: 88.0%

(2R,3R,4R,5S)-Benzyl 3,4-bis(benzyloxy)-2-(4-(benzyloxy)-phenyl)-5-(trityloxymethyl)pyrrolidine-1-carboxylate (1615251-25-6) → (2S,3R,4R,5R)-2-(Hydroxymethyl)-5-(4-hydroxyphenyl)-pyrrolidine-3,4-diol

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c4ob00503a

Downstream raw materials:

(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-1-methyl-5-(trityloxymethyl)pyrrolidine

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