(1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester
• CAS No.: 222967-30-8
• Molecular Formula: C₂₆H₂₆O₈
• Molecular Weight: 466.488

Synonyms:(1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester

Chemical Property of (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester

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Technology Process of (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester

There total 4 articles about (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.0^2,4]oct-6-ene-6,7-dicarboxylic acid dimethyl 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: 76.0%

(1S,4R)-1,4-Bis-benzyloxymethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester (222967-29-5) → (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester (222967-30-8)

Guidance literature:

With Santonox R; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 80 ℃; for 0.666667h;

DOI:10.1016/S0040-4039(99)00256-7

Reference yield:

2,5-bis-(hydroxymethyl)furan (1883-75-6) → (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester (222967-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaH; Bu₄NI / tetrahydrofuran / 2.5 h / 67 °C

2: 83 percent / toluene / 10 h / 110 °C

3: 76 percent / MCPBA; 4,4'-thiobis(2-tert-butyl-5-methylphenol) / 1,2-dichloro-ethane / 0.67 h / 80 °C

With Santonox R; tetra-(n-butyl)ammonium iodide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; 1: Etherification / 2: Cycloaddition / 3: Epoxidation;

DOI:10.1016/S0040-4039(99)00256-7

Reference yield:

benzyl bromide (100-39-0) → (1R,2R,4S,5S)-1,5-Bis-benzyloxymethyl-3,8-dioxa-tricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylic acid dimethyl ester (222967-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaH; Bu₄NI / tetrahydrofuran / 2.5 h / 67 °C

2: 83 percent / toluene / 10 h / 110 °C

3: 76 percent / MCPBA; 4,4'-thiobis(2-tert-butyl-5-methylphenol) / 1,2-dichloro-ethane / 0.67 h / 80 °C

With Santonox R; tetra-(n-butyl)ammonium iodide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dichloro-ethane; toluene; 1: Etherification / 2: Cycloaddition / 3: Epoxidation;

DOI:10.1016/S0040-4039(99)00256-7

upstream raw materials:

(1S,4R)-1,4-Bis-benzyloxymethyl-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

2,5-bis-(hydroxymethyl)furan

benzyl bromide

2,5-Bis-benzyloxymethyl-furan

Downstream raw materials:

(1R,2R,4S,5S,6R,7S)-1,5-Bis-benzyloxymethyl-6,7-dihydroxy-3,8-dioxa-tricyclo[3.2.1.0^2,4]octane-6,7-dicarboxylic acid dimethyl ester

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