Cyclopentanone, 4-acetyl-3-(hydroxymethyl)-2-methyl-2-[(phenylmethoxy)methyl]-, (2R,3R,4S)-

Base Information

• Chemical Name: Cyclopentanone, 4-acetyl-3-(hydroxymethyl)-2-methyl-2-[(phenylmethoxy)methyl]-, (2R,3R,4S)-
• CAS No.: 213816-86-5
• Molecular Formula: C17H22O4
• Molecular Weight: 290.359
• Mol file: 213816-86-5.mol

Synonyms:

Chemical Property of Cyclopentanone, 4-acetyl-3-(hydroxymethyl)-2-methyl-2-[(phenylmethoxy)methyl]-, (2R,3R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopentanone, 4-acetyl-3-(hydroxymethyl)-2-methyl-2-[(phenylmethoxy)methyl]-, (2R,3R,4S)-

There total 17 articles about Cyclopentanone, 4-acetyl-3-(hydroxymethyl)-2-methyl-2-[(phenylmethoxy)methyl]-, (2R,3R,4S)- 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: 97.0%

(2R,3R,4S)-4-acetyl-2-(benzyloxy)methyl-3-((tert-butyldimethylsilanyl)oxymethyl)-2-methylcyclopentanone (213816-66-1) → (2R,3R,4S)-4-Acetyl-2-benzyloxymethyl-3-hydroxymethyl-2-methyl-cyclopentanone (213816-86-5)

Guidance literature:

With water; acetic acid; Ambient temperature;

DOI:10.1016/S0040-4039(98)01385-9

Reference yield:

Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-4-hydroxy-6-hydroxymethyl-5-methyl-bicyclo[2.2.1]hept-2-yl ester (213816-83-2) → (2R,3R,4S)-4-Acetyl-2-benzyloxymethyl-3-hydroxymethyl-2-methyl-cyclopentanone (213816-86-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: 100 percent / K₂CO₃ / methanol / 2 h / 20 °C

3: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH₂Cl₂ / 2 h / 20 °C

4: 86 percent / NaH; 15-crown-5 / toluene / 1 h / 20 °C

5: 97 percent / CH₃COOH / H₂O / 5 h / 20 °C

With 1H-imidazole; 15-crown-5; 4 A molecular sieve; sodium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(02)01474-6

Reference yield:

[(1R,2R,3R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-bicyclo[2.2.1]hept-2-yl]-methanol (213816-80-9) → (2R,3R,4S)-4-Acetyl-2-benzyloxymethyl-3-hydroxymethyl-2-methyl-cyclopentanone (213816-86-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / NaH / dimethylformamide / 12 h / 20 °C

2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3: 99 percent / pyridine / 10 h / 20 °C

4: 80 percent / CH₃COOH / H₂O / 12 h / 65 °C

5: NaIO₄; (NH₄)2SO₄ / methanol; H₂O / 0.25 h / 0 °C

6: 13 g / NaBH₄ / methanol; H₂O / 0.08 h / 0 °C

7: 96 percent / imidazole / dimethylformamide / 5 h / 20 °C

8: 100 percent / K₂CO₃ / methanol / 2 h / 20 °C

9: 90 percent / pyridinium chlorochromate; molecular sieves 4 Amgstroem / CH₂Cl₂ / 2 h / 20 °C

10: 86 percent / NaH; 15-crown-5 / toluene / 1 h / 20 °C

11: 97 percent / CH₃COOH / H₂O / 5 h / 20 °C

With pyridine; 1H-imidazole; ammonium sulfate; sodium tetrahydroborate; sodium periodate; 15-crown-5; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(02)01474-6

upstream raw materials:

(2R,3R,4S)-4-acetyl-2-(benzyloxy)methyl-3-((tert-butyldimethylsilanyl)oxymethyl)-2-methylcyclopentanone

benzyl bromide

(S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester

Acetic acid (1S,2S,4R,5R,6R)-5-benzyloxymethyl-4-hydroxy-6-hydroxymethyl-5-methyl-bicyclo[2.2.1]hept-2-yl ester

Downstream raw materials:

3R,4R-epoxy-13-keto-1R,11S-dolabell-7E,12⁽¹⁸⁾-diene

[(1R,2R,5S)-2-Benzyloxymethyl-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-cyclopent-3-enyl]-methanol

((1R,2R,5S)-2-(benzyloxy)methyl-2-methyl-5-(2-methyl-1,3-dioxolan-2-yl)cyclopent-3-enyl)methyl acetate

Acetic acid (1R,2R,5S)-2-benzyloxymethyl-3-hydroxy-2-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-cyclopentylmethyl ester