(R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone

Base Information

• Chemical Name: (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone
• CAS No.: 92081-33-9
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.288
• Mol file: 92081-33-9.mol

Synonyms:

Chemical Property of (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone

There total 10 articles about (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-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:

(Z)-(S)-4-[(4R,5S)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-4-methoxy-but-2-enoic acid ethyl ester (92081-26-0) → (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone (92081-33-9)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TosH / acetone / Heating

2: pTosH / toluene / Heating

3: H₃O⁽¹⁺⁾

4: pyridine

5: 83 percent / chlorobenzene / 72 h / 125 °C

6: Jones reagent

7: K₂CO₃ / H₂O; tetrahydrofuran

8: H⁽¹⁺⁾

With jones reagent; oxonium; hydrogen cation; potassium carbonate; toluene-4-sulfonic acid; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; water; chlorobenzene; acetone; toluene;

DOI:10.1016/S0040-4039(01)81199-0

Reference yield:

(5S,6S)-6-((1S,2R)-1,2-Dihydroxy-propyl)-5-methoxy-5,6-dihydro-pyran-2-one → (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone (92081-33-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: 83 percent / chlorobenzene / 72 h / 125 °C

3: Jones reagent

4: K₂CO₃ / H₂O; tetrahydrofuran

5: H⁽¹⁺⁾

With jones reagent; hydrogen cation; potassium carbonate; In tetrahydrofuran; pyridine; water; chlorobenzene;

DOI:10.1016/S0040-4039(01)81199-0

Reference yield:

Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S)-3-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl ester (92081-29-3) → (R)-5-((1S,3S,4R)-2,3,4-Trihydroxy-1-methoxy-pentyl)-cyclohex-2-enone (92081-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / chlorobenzene / 72 h / 125 °C

2: Jones reagent

3: K₂CO₃ / H₂O; tetrahydrofuran

4: H⁽¹⁺⁾

With jones reagent; hydrogen cation; potassium carbonate; In tetrahydrofuran; water; chlorobenzene;

DOI:10.1016/S0040-4039(01)81199-0

upstream raw materials:

(5S,6R)-5-Methoxy-6-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-5,6-dihydro-pyran-2-one

(Z)-(4S,5R)-5-Hydroxy-4-methoxy-5-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pent-2-enoic acid ethyl ester

Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S)-3-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-propyl ester

Acetic acid (1S,2R)-2-acetoxy-1-((3R,4S,4aR,8aR)-4-methoxy-1,8-dioxo-3,4,4a,5,8,8a-hexahydro-1H-isochromen-3-yl)-propyl ester

Downstream raw materials:

(R)-5-[(S)-1-Methoxy-2-oxo-2-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-ethyl]-cyclohex-2-enone

(R)-5-[(S)-2-Hydroxy-1-methoxy-2-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-ethyl]-cyclohex-2-enone