(3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate

Base Information

• Chemical Name: (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate
• CAS No.: 1117906-44-1
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.207

Synonyms:(3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate

Chemical Property of (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate

There total 3 articles about (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate 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:

(3aS,4S,7R,7aR)-methyl 4-methoxy-7-(methoxymethoxy)-2,2-di-methyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate → (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate (1117906-44-1)

Guidance literature:

With methanol; trifluoroacetic acid; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2011.10.135

Reference yield:

(3aS,4S,7R,7aR)-methyl 4-hydroxy-7-(methoxymethoxy)-2,2-di-methyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate → (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate (1117906-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfide; silver(l) oxide / tetrahydrofuran / 3 h / 20 °C / Darkness

2: methanol; trifluoroacetic acid / 24 h / 0 - 20 °C

With methanol; dimethylsulfide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2011.10.135

Reference yield:

methyl 2-(hydroxy((4S,5R)-5-((R)-1-(methoxymethoxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)acrylate → (3R,4R,5R,6S)-methyl 3,4,5-trihydroxy-6-methoxycyclohex-1-ene-carboxylate (1117906-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 30 h / Reflux

2: dimethylsulfide; silver(l) oxide / tetrahydrofuran / 3 h / 20 °C / Darkness

3: methanol; trifluoroacetic acid / 24 h / 0 - 20 °C

With methanol; Hoveyda-Grubbs catalyst second generation; dimethylsulfide; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2011.10.135

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