(4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone

Base Information

• Chemical Name: (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone
• CAS No.: 1413333-82-0
• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.277

Synonyms:(4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone

Chemical Property of (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone

Chemical Property:

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Technology Process of (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone

There total 3 articles about (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone 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: 74.0%

(4R,5R,7R,8R)-4-hydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-7,8-dimethoxy-7,8-dimethyl-6,9-dioxaspiro[4.5]dec-2-en-1-one (1413333-10-4) → (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone (1413333-82-0)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 3h; Sonication;

DOI:10.1002/hlca.201200421

Reference yield:

(2R,5R,6R,5'R)-5'-hydroxy-2'-oxospiropent-3'-ene-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane (1042926-22-6) → (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone (1413333-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tributylphosphine; phenol / tetrahydrofuran / 24 h / 15 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / water / 3 h / 20 °C / Sonication

With tributylphosphine; trifluoroacetic acid; phenol; In tetrahydrofuran; water; 1: |Morita-Baylis-Hillman Alkylation;

DOI:10.1002/hlca.201200421

Reference yield:

3-methoxy-benzaldehyde (591-31-1) → (4R,5R)-4,5-dihydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-5-(hydroxymethyl)cyclopent-2-enone (1413333-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tributylphosphine; phenol / tetrahydrofuran / 24 h / 15 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / water / 3 h / 20 °C / Sonication

With tributylphosphine; trifluoroacetic acid; phenol; In tetrahydrofuran; water; 1: |Morita-Baylis-Hillman Alkylation;

DOI:10.1002/hlca.201200421

upstream raw materials:

(2R,5R,6R,5'R)-5'-hydroxy-2'-oxospiropent-3'-ene-5,6-dimethoxy-5,6-dimethyl-[1,4]dioxane

(4R,5R,7R,8R)-4-hydroxy-2-[(R)-hydroxy(3-methoxyphenyl)methyl]-7,8-dimethoxy-7,8-dimethyl-6,9-dioxaspiro[4.5]dec-2-en-1-one

3-methoxy-benzaldehyde

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