cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)

Base Information

• Chemical Name: cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)
• CAS No.: 339291-60-0
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386

Synonyms:cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)

Chemical Property of cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)

Chemical Property:

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Technology Process of cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)

There total 2 articles about cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R) 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-methoxybenzaldehyde diethylacetal (2403-58-9) + ((2R,3R)-3-Hydroxy-2-hydroxymethyl-1-methyl-cyclopentyl)-acetic acid methyl ester → cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R) (339291-60-0)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃; for 3h; under 10 - 15 Torr;

DOI:10.1021/jo005683f

Reference yield:

cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2,5-dimethyl-, ethyl ester, (2S,4aR,5RS,7aR) → cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R) (339291-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / methanol / 13 h / Heating

2: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

With toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo005683f

Reference yield: 83.0%

cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R) (339291-60-0) → 2-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-ethanol (339291-61-1)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; cyclohexane; at -78 ℃; for 5h;

DOI:10.1021/jo005683f

upstream raw materials:

4-methoxybenzaldehyde diethylacetal

Downstream raw materials:

2-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-ethanol

(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

(Z)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester

(2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienal

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