(+)-(R)-manoalide

Base Information

• Chemical Name: (+)-(R)-manoalide
• CAS No.: 540482-87-9
• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.558
• Mol file: 540482-87-9.mol

Synonyms:(+)-(R)-manoalide

Chemical Property of (+)-(R)-manoalide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(R)-manoalide

There total 11 articles about (+)-(R)-manoalide 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: 60.0%

(+)-(2RS,6R)-3-[(E)-4'-methyl-6'-(2'',6'',6''-trimethylcyclohex-1''-enyl)hex-3'-enyl]-6-(5'''-triethylsilanylfuran-3'''-yl)-5,6-dihydro-2H-pyran-2-ol → (+)-(R)-manoalide (540482-87-9)

Guidance literature:

With oxygen; rose bengal; In methanol; at -78 ℃; for 0.25h; Irradiation;

DOI:10.1021/jo0268097

Reference yield:

(R)-6-Furan-3-yl-3-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-5,6-dihydro-2H-pyran-2-ol (261522-05-8) → (+)-(R)-manoalide (540482-87-9)

Guidance literature:

With oxygen; In dichloromethane; at -78 ℃; Irradiation;

DOI:10.1016/S0957-4166(99)00529-7

Reference yield:

(E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol (110202-07-8) → (+)-(R)-manoalide (540482-87-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / triphenylphosphine; imidazole; iodine / CH₂Cl₂ / 2 h / 20 °C

2: 91 percent / Pd(PPh₃)4; iPr₂NEt / tetrahydrofuran; methanol / 24 h / 65 - 70 °C

3: 89 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

4: 60 percent / oxygen; Rose Bengal / methanol / 0.25 h / -78 °C / Irradiation

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; oxygen; rose bengal; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jo0268097

upstream raw materials:

seco-manoalide

(R)-6-Furan-3-yl-3-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-5,6-dihydro-2H-pyran-2-ol

(E)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol

2-[(E)-6-iodo-3-methylhex-3-enyl]-1,3,3-trimethylcyclohexene

Downstream raw materials:

luffariolide B

manoalide 25-acetals diacetate

manoalide 25-acetal monoacetate