(2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Base Information

• Chemical Name: (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
• CAS No.: 262284-21-9
• Molecular Formula: C₃₇H₅₂O₄Se
• Molecular Weight: 639.777
• Mol file: 262284-21-9.mol

Synonyms:

Chemical Property of (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

There total 3 articles about (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 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: 62.0%

myristylaldehyde (124-25-4,511542-15-7) + methyllithium (917-54-4) + (Z)-2-Phenylselanyl-but-2-enedioic acid bis-((1R,2S)-2-phenyl-cyclohexyl) ester (262284-18-4) → (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (262284-21-9)

Guidance literature:

methyllithium; (Z)-2-Phenylselanyl-but-2-enedioic acid bis-((1R,2S)-2-phenyl-cyclohexyl) ester; In tetrahydrofuran; at -78 ℃; for 0.166667h;

myristylaldehyde; In tetrahydrofuran; dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1016/S0040-4039(99)02119-X

Reference yield:

diphenyl diselenide (1666-13-3) → (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (262284-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / n-Bu₃P; H₂O / acetonitrile / 1 h / 0 °C

2.1: tetrahydrofuran; various solvent(s) / 0.17 h / -78 °C

2.2: 62 percent / CH₂Cl₂; tetrahydrofuran; various solvent(s) / 0.5 h / -40 °C

With tributylphosphine; water; In tetrahydrofuran; acetonitrile; 1.1: Addition / 2.1: Methylation / 2.2: Addition;

DOI:10.1016/S0040-4039(99)02119-X

Reference yield:

But-2-ynedioic acid bis-((1R,2S)-2-phenyl-cyclohexyl) ester (262284-17-3) → (2S,3R,4S)-4-Methyl-5-oxo-3-phenylselanyl-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (262284-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / n-Bu₃P; H₂O / acetonitrile / 1 h / 0 °C

2.1: tetrahydrofuran; various solvent(s) / 0.17 h / -78 °C

2.2: 62 percent / CH₂Cl₂; tetrahydrofuran; various solvent(s) / 0.5 h / -40 °C

With tributylphosphine; water; In tetrahydrofuran; acetonitrile; 1.1: Addition / 2.1: Methylation / 2.2: Addition;

DOI:10.1016/S0040-4039(99)02119-X

upstream raw materials:

myristylaldehyde

methyllithium

(Z)-2-Phenylselanyl-but-2-enedioic acid bis-((1R,2S)-2-phenyl-cyclohexyl) ester

diphenyl diselenide

Downstream raw materials:

(+)-roccellaric acid

(2S,3R,4R)-4-Methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

(2S,3S,4R)-4-Methyl-5-oxo-2-tridecyl-tetrahydro-furan-3-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester