(1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane

Base Information

• Chemical Name: (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane
• CAS No.: 121542-20-9
• Molecular Formula: C₁₉H₂₃NO₆
• Molecular Weight: 361.395

Synonyms:(1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane

Chemical Property of (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane

Chemical Property:

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Technology Process of (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane

There total 2 articles about (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane 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:

(2R,3S,4S,5S)-1-Benzyl-2,5-bis<(ethoxycarbonyl)methyl>-3,4-bis<(trimethylsilyl)oxy>pyrrolidine (121542-18-5) → (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane (121542-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₄NF / tetrahydrofuran / 0.83 h / 0 °C

2: DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00075a024

Reference yield:

acetic anhydride (108-24-7) + (1R,3S,4S,5S)-2-Benzyl-3-<(ethoxycarbonyl)methyl>-4-hydroxy-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane (121542-19-6) → (1R,3S,4S,5S)-4-Acetoxy-2-benzyl-3-<(ethoxycarbonyl)methyl>-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane (121542-20-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1021/ja00194a078

upstream raw materials:

acetic anhydride

(1R,3S,4S,5S)-2-Benzyl-3-<(ethoxycarbonyl)methyl>-4-hydroxy-2-aza-6-oxa-7-oxobicyclo<3.3.0>octane

(2R,3S,4S,5S)-1-Benzyl-2,5-bis<(ethoxycarbonyl)methyl>-3,4-bis<(trimethylsilyl)oxy>pyrrolidine

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