(4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone

Base Information

• Chemical Name: (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone
• CAS No.: 1373332-57-0
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• Mol file: 1373332-57-0.mol

Synonyms:(4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone

Chemical Property of (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone

There total 7 articles about (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone 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: 59.0%

(1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol (681853-99-6) → (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone (1373332-57-0) + (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Molecular sieve;

DOI:10.1021/jm3004009

Reference yield:

(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol (1067238-45-2) → (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone (1373332-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 80 °C / Inert atmosphere

2: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h / 20 °C / Molecular sieve

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dipyridinium dichromate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm3004009

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (4R,5R)3-[(benzoyloxy)methyl]-4,5-O-isopropylidene-2-cyclopentenone (1373332-57-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole

2.1: potassium tert-butylate / tetrahydrofuran

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 20 °C

4.1: tetrahydrofuran / -78 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: toluene / 3 h / Inert atmosphere; Reflux

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 4 h / 80 °C / Inert atmosphere

8.1: dipyridinium dichromate / N,N-dimethyl-formamide / 48 h / 20 °C / Molecular sieve

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dipyridinium dichromate; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Wittig reaction / 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1021/jm3004009

upstream raw materials:

(2R,3S,4S)-3,4-(O-isopropylidenedioxy)-2-vinyl-hexan-5-en-1,2-diol

(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

2,3-O-isopropylidene-D-ribofuranose

D-Ribose