(2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol

Base Information

• Chemical Name: (2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol
• CAS No.: 1151811-07-2
• Molecular Formula: C₂₃H₂₉NO₃
• Molecular Weight: 367.488

Synonyms:(2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol

Chemical Property of (2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol

Chemical Property:

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Technology Process of (2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol

There total 1 articles about (2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol 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:

C32H45NO8S → (2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol (1151811-07-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1039/b821431j

Reference yield: 94.0%

(2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol (1151811-07-2) + 1,1'-carbonyldiimidazole (530-62-1) → (5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(but-3-enyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one (1151811-08-3)

Guidance literature:

With dmap; In toluene; for 3h; Inert atmosphere; Reflux;

DOI:10.1039/b821431j

Reference yield: 93.0%

(2R,3R,4R,5R)-[3,4-bis(benzyloxy)-5-(but-3-enyl)pyrrolidin-2-yl]methanol (1151811-07-2) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl [(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(but-3-enyl)-5-(hydroxymethyl)]pyrrolidine-1-carboxylate (1187972-10-6)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.046

Downstream raw materials:

tert-butyl [(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(but-3-enyl)-5-(hydroxymethyl)]pyrrolidine-1-carboxylate

benzyl [(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(but-3-enyl)-5-(hydroxymethyl)]pyrrolidine-1-carboxylate

(5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(but-3-enyl)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

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