2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI)

Base Information

• Chemical Name: 2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI)
• CAS No.: 672948-80-0
• Molecular Formula: C7H10O4
• Molecular Weight: 158.15
• Mol file: 672948-80-0.mol

Synonyms:2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI)

Chemical Property of 2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI)

There total 24 articles about 2-Cyclopenten-1-one, 4,5-dihydroxy-4-[(1R)-1-hydroxyethyl]-, (4R,5S)-rel- (9CI) 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: 42.0%

(3aR,6aS)-6a-((R)-1-Methoxymethoxy-ethyl)-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (672337-39-2) → (+)-pentenocin B (672948-80-0,672948-82-2,672948-79-7,677751-80-3,677751-81-4,677751-78-9)

Guidance literature:

With trifluoroacetic acid; In water; at 0 ℃; for 2h;

DOI:10.1021/jo035430x

Reference yield: 30.0%

(3aR,6aS)-6a-((S)-1-Methoxymethoxy-ethyl)-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (902775-81-9) → 6-epi-pentenocin B (672948-80-0,672948-82-2,672948-79-7,677751-80-3,677751-81-4,677751-78-9)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.04.054

Reference yield:

(-)-(1R,2R,6R,7S)-tricyclo[5.2.1.02,6]deca-4,8-dien-3-one (111136-75-5) → (+)-pentenocin B (672948-80-0,672948-82-2,672948-79-7,677751-80-3,677751-81-4,677751-78-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / CuI / tetrahydrofuran / 0.5 h / -35 °C

2: 84 percent / CuCl; O₂ / PdCl₂ / dimethylformamide; H₂O / 10 h / 50 °C

3: 73 percent / p-TsOH; DDQ / dioxane / 20 h / Heating

4: 66 percent / DIBALH / tetrahydrofuran; toluene / 0.25 h / -78 °C

5: 97 percent / NBS / tetrahydrofuran / 0.25 h / -15 °C

6: 91 percent / iPr₂NEt / CH₂Cl₂ / 10 h / 20 °C

7: 61 percent / 4-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 96 h / 20 °C

8: 75 percent / p-TsOH / CH₂Cl₂ / 17 h / 20 °C

9: 100 percent / Zn; AcOH / methanol / 1 h / 50 °C

10: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

11: 98 percent / diphenyl ether / 0.25 h / 280 °C

12: 42 percent / TFA / H₂O / 2 h / 0 °C

With N-Bromosuccinimide; copper(l) iodide; osmium(VIII) oxide; oxalyl dichloride; oxygen; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; zinc; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; diphenylether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 10: Swern oxidation;

DOI:10.1021/jo035430x

upstream raw materials:

(3aR,6aS)-6a-((R)-1-Methoxymethoxy-ethyl)-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

(-)-(1R,2R,6R,7S)-tricyclo[5.2.1.0^2,6]deca-4,8-dien-3-one

(3aS,4R,7S,7aR)-3-Acetyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one

(3R,3aS,4R,7S,7aR)-3-Vinyl-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one