Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester

Base Information

• Chemical Name: Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester
• CAS No.: 460745-70-4
• Molecular Formula: C₁₆H₁₅NO₇
• Molecular Weight: 333.298

Synonyms:Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester

Chemical Property of Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester

Chemical Property:

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Technology Process of Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester

There total 3 articles about Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester 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:

4-methoxy-benzylamine (2393-23-9) + acetyl chloride (75-36-5) + (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (27750-13-6) → Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester (460745-70-4)

Guidance literature:

acetyl chloride; (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid; for 2h; Heating;

4-methoxy-benzylamine; In tetrahydrofuran; at 20 ℃; for 4h;

With acetyl chloride; for 18h; Heating;

DOI:10.1016/S0040-4039(02)02781-8

Reference yield:

(2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (27750-13-6) → Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester (460745-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Reflux

2.1: tetrahydrofuran / 5 h / 0 - 20 °C

2.2: 10 h / Reflux

In tetrahydrofuran;

DOI:10.1021/acs.jnatprod.0c00211

Reference yield:

(3aS,6aS)-2,4,6-trioxohexahydrofuro[3,4-b]furan-3a-yl acetate + 4-methoxy-benzylamine (2393-23-9) → Acetic acid (3aS,6aS)-5-(4-methoxy-benzyl)-2,4,6-trioxo-hexahydro-furo[2,3-c]pyrrol-3a-yl ester (460745-70-4)

Guidance literature:

(3aS,6aS)-2,4,6-trioxohexahydrofuro[3,4-b]furan-3a-yl acetate; 4-methoxy-benzylamine; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

With acetyl chloride; for 10h; Reflux;

DOI:10.1021/acs.jnatprod.0c00211

upstream raw materials:

4-methoxy-benzylamine

acetyl chloride

(2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid

Downstream raw materials:

(3aS,6aS)-3a-hydroxy-5-(4-methoxybenzyl)dihydro-2H-furo[2,3-c]pyrrole-2,4,6(5H,6aH)-trione

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