(3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one

Base Information

• Chemical Name: (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one
• CAS No.: 1438281-02-7
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32

Synonyms:(3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one

Chemical Property of (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one

Chemical Property:

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Technology Process of (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one

There total 2 articles about (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one 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: 95.0%

(R)-5-((S)-hydroxy((R)-1-((S)-1-phenylethyl)aziridin-2-yl)methyl)-furan-2(5H)-one (1438281-01-6) → (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one (1438281-02-7)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; for 15h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c3ob27390c

Reference yield:

(R)-1-((S)-1-phenylethyl)aziridine-2-carbaldehyde (182370-58-7) → (3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one (1438281-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc dibromide / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

1.2: 1.5 h / 0 °C / Inert atmosphere

2.1: trifluoroacetic acid / tetrahydrofuran; water / 15 h / Inert atmosphere

With trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; water;

DOI:10.1039/c3ob27390c

Reference yield: 90.0%

(3aS,5R,6S,6aR)-6-hydroxy-5-(hydroxymethyl)-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-2-one (1438281-02-7) + 4-nitro-benzoyl chloride (122-04-3) → ((3aS,5R,6S,6aR)-6-((4-nitrobenzoyl)oxy)-2-oxo-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-5-yl)methyl 4-nitrobenzoate (1438281-03-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c3ob27390c

upstream raw materials:

(R)-1-((S)-1-phenylethyl)aziridine-2-carbaldehyde

(R)-5-((S)-hydroxy((R)-1-((S)-1-phenylethyl)aziridin-2-yl)methyl)-furan-2(5H)-one

Downstream raw materials:

((3aS,5R,6S,6aR)-6-((4-nitrobenzoyl)oxy)-2-oxo-4-((S)-1-phenylethyl)hexahydro-2H-furo[3,2-b]pyrrol-5-yl)methyl 4-nitrobenzoate

(2S,3R,4S,5R)-2-(2-hydroxyethyl)-5-(hydroxymethyl)-1-((S)-1-phenylethyl)pyrrolidine-3,4-diol

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