(2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol

Base Information

• Chemical Name: (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol
• CAS No.: 1018472-25-7
• Molecular Formula: C₂₂H₂₉NO₅
• Molecular Weight: 387.476
• Mol file: 1018472-25-7.mol

Synonyms:(2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol

Chemical Property of (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol

There total 2 articles about (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol 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: 80.0%

(7S,7aR)-1-((1S,2S)-1,2-bis(benzyloxy)-3-hydroxypropyl)-tetrahydro-7-hydroxypyrrolo[1,2-c]oxazol-3(1H)-one (1018472-23-5) → (2R,3S)-2-((2R,3S,4S)-3,4-bis(benzyloxy)-tetrahydrofuran-2-yl)pyrrolidin-3-ol (1018472-27-9) + (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol (1018472-25-7)

Guidance literature:

With sodium hydroxide; In methanol; at 110 ℃; for 2h; microwave irradiation;

DOI:10.1016/j.tet.2008.01.073

Reference yield: 63.0%

5-(2,3-bisbenzyloxy-1,4-diacetoxybutyl)-4-acetoxypyrrolidin-2-one (1235303-62-4) → (2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol (1018472-25-7)

Guidance literature:

5-(2,3-bisbenzyloxy-1,4-diacetoxybutyl)-4-acetoxypyrrolidin-2-one; With dimethylsulfide borane complex; In tetrahydrofuran; for 10h; Reflux;

With hydrogenchloride; water; In methanol; at 20 ℃; for 0.5h;

DOI:10.1002/chem.200903490

Reference yield: 25.0%

(2S,3S)-2-((1R,2S,3S)-2,3-bis(benzyloxy)-1,4-dihydroxybutyl)pyrrolidin-3-ol (1018472-25-7) → (3aS,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydro-1H-oxepino-[3,2-b]pyrrol-8-ol (1018472-31-5) + (2R,3S)-2-((2R,3S,4S)-3,4-bis(benzyloxy)-tetrahydrofuran-2-yl)pyrrolidin-3-ol (1018472-27-9) + (1S,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydroindolizine-1,8-diol (1018472-29-1)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 5 ℃; for 12h;

DOI:10.1016/j.tet.2008.01.073

upstream raw materials:

(7S,7aR)-1-((1S,2S)-1,2-bis(benzyloxy)-3-hydroxypropyl)-tetrahydro-7-hydroxypyrrolo[1,2-c]oxazol-3(1H)-one

5-(2,3-bisbenzyloxy-1,4-diacetoxybutyl)-4-acetoxypyrrolidin-2-one

Downstream raw materials:

(3aS,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydro-1H-oxepino-[3,2-b]pyrrol-8-ol

(2R,3S)-2-((2R,3S,4S)-3,4-bis(benzyloxy)-tetrahydrofuran-2-yl)pyrrolidin-3-ol

(1S,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydroindolizine-1,8-diol