5-hydroxy-5-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl acetate

Base Information

• Chemical Name: 5-hydroxy-5-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl acetate
• CAS No.: 68907-80-2
• Molecular Formula: C8H10O5
• Molecular Weight: 186.162
• Mol file: 68907-80-2.mol

Synonyms:

Chemical Property of 5-hydroxy-5-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl acetate

Chemical Property:

• Vapor Pressure: 5.99E-06mmHg at 25°C
• Boiling Point: 339.8°C at 760 mmHg
• Flash Point: 139.7°C
• Density: 1.4g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-hydroxy-5-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl acetate

There total 12 articles about 5-hydroxy-5-(hydroxymethyl)-4-oxocyclopent-2-en-1-yl acetate 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: 88.0%

t-4-acetoxy-5-hydroxy-r-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone (68882-75-7) → (+/-)-pentenomycin II (68907-80-2,57172-42-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; for 162h; Ambient temperature;

DOI:10.1021/jo00349a009

Reference yield:

6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene (80963-24-2) → (+/-)-pentenomycin II (68907-80-2,57172-42-6)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL / toluene / 7 h / -78 °C

2: oxalic acid / CH₂Cl₂; H₂O / 3.5 h / Ambient temperature

3: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature

4: 1.) OsO₄, 2.) aq. NaHSO₃ / 1.) a) pyridine, 0-5 deg C, b) RT, 5 h, 2.) pyridine, RT, 3 h

5: 94 percent / pyridine / 10 h / 4 °C

6: 67 percent / SeO₂ / 2-methyl-propan-2-ol; benzene / Heating

7: 88 percent / acetic acid (glacial) / tetrahydrofuran; H₂O / 162 h / Ambient temperature

With pyridine; 1H-imidazole; osmium(VIII) oxide; selenium(IV) oxide; oxalic acid; diisobutylaluminium hydride; sodium hydrogensulfite; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/jo00349a009

Reference yield:

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1) → (+/-)-pentenomycin II (68907-80-2,57172-42-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, 2.) / 1.) THF, -78 deg C, 2.) -78 deg C

2: DIBAL / toluene / 7 h / -78 °C

3: oxalic acid / CH₂Cl₂; H₂O / 3.5 h / Ambient temperature

4: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature

5: 1.) OsO₄, 2.) aq. NaHSO₃ / 1.) a) pyridine, 0-5 deg C, b) RT, 5 h, 2.) pyridine, RT, 3 h

6: 94 percent / pyridine / 10 h / 4 °C

7: 67 percent / SeO₂ / 2-methyl-propan-2-ol; benzene / Heating

8: 88 percent / acetic acid (glacial) / tetrahydrofuran; H₂O / 162 h / Ambient temperature

With pyridine; 1H-imidazole; osmium(VIII) oxide; n-butyllithium; selenium(IV) oxide; oxalic acid; diisobutylaluminium hydride; sodium hydrogensulfite; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/jo00349a009

upstream raw materials:

t-4-acetoxy-5-hydroxy-r-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-cyclopentenone

6-carbethoxy-1,4-dioxaspiro<4.4>non-6-ene

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene

2-bromo-2-cyclopenten-1-one

Refernces