Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]-

Base Information

• Chemical Name: Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]-
• CAS No.: 150097-18-0
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 150097-18-0.mol

Synonyms:Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]-

Chemical Property of Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]-

There total 26 articles about Ethanone, 1-(tetrahydro-5-hydroxy-3,4-dimethyl-3-furanyl)-, [3R-(3alpha,4alpha,5beta)]- 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:

(2R,3R,4S,5S)-4-<(1S)-1-(hydroxymethyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-25-8,119363-74-5) → (2RS,3S,4R)-4-acetyl-3,4-dimethyltetrahydro-2-furanol (150097-17-9,150097-18-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / pyridine / 3 h / Ambient temperature

2: 93 percent / 60percent aq. acetic acid / 24 h / Ambient temperature

3: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, -78 deg C, 1 h

4: aq. NaIO₄ / methanol / 3.5 h / 0 °C

5: BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -15 °C

6: 69 percent / Raney nickel / ethanol / 3 h / Heating

7: 88 percent / 60percent aq. trifluoroacetic acid / 7.5 h / 5 °C

8: aq. NaIO₄ / methanol / 2.5 h / Ambient temperature

9: 1.) NaBH₄, 2.) 35percent aq. H₂O₂, 3.) 1 M aq. NaOH

10: 99 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

11: 90 percent / DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

12: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

13: 60percent aq. AcOH / 3 h / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; nickel; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triphenylphosphine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.66.1441

Reference yield:

(2R,3R,4S,5S)-4-<(1R)-1-(hydroxymethyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-25-8,119363-74-5) → (2RS,3R,4R)-4-acetyl-3,4-dimethyltetrahydro-2-furanol (150097-17-9,150097-18-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / pyridine / 3 h / Ambient temperature

2: 96 percent / 60percent aq. acetic acid / 24 h / Ambient temperature

3: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, -78 deg C, 1 h

4: aq. NaIO₄ / methanol / 3.5 h / 0 °C

5: BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -15 °C

6: 77 percent / Raney nickel / ethanol / 3 h / Heating

7: 85 percent / 60percent aq. trifluoroacetic acid / 7.5 h / 5 °C

8: aq. NaIO₄ / methanol / 2.5 h / Ambient temperature

9: 1.) NaBH₄, 2.) 35percent aq. H₂O₂, 3.) 1 M aq. NaOH

10: 86 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

11: 98 percent / DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

12: oxalyl dichloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

13: 60percent aq. AcOH / 3 h / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; nickel; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triphenylphosphine; trifluoroacetic acid; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.66.1441

Reference yield:

(2S,3R,4R)-2,3-dimethyl-3-<(t-butyldimethylsilyloxy)methyl>-1,4-pentanediol (150097-14-6) → (2RS,3S,4R)-4-acetyl-3,4-dimethyltetrahydro-2-furanol (150097-17-9,150097-18-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

2: 60percent aq. AcOH / 3 h / Ambient temperature

With oxalyl dichloride; acetic acid; dimethyl sulfoxide; In dichloromethane;

DOI:10.1246/bcsj.66.1441

upstream raw materials:

(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dimethyl-4-oxo-pentanal

(2R,3R,4S,5S)-4-<(1S)-1-(hydroxymethyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

(2S,3R,4R)-2,3-dimethyl-3-<(t-butyldimethylsilyloxy)methyl>-1,4-pentanediol

(2R,3R)-2-methyl-2-<(S)-1-methyl-2-(pivaloyloxy)ethyl>-1,3-butanediol