(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester

Base Information

• Chemical Name: (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester
• CAS No.: 662168-55-0
• Molecular Formula: C₃₈H₅₀O₄
• Molecular Weight: 570.813
• Mol file: 662168-55-0.mol

Synonyms:(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester

Chemical Property of (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester

There total 14 articles about (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl 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: 84.0%

(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-hydroxy-(5R)-methyl-(1R)-propylhexyl ester (662168-63-0) → (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester (662168-55-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.25h;

DOI:10.1021/ja039716v

Reference yield:

1-bromo-3-phenylprop-2-yne (1794-48-5) → (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester (662168-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 2.25 h / -78 - 0 °C

2.1: 79 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3.1: 96 percent / imidazole / dimethylformamide / 20 h / 23 °C

4.1: 81 percent / Ni(cod)2; PBu₃; Et₃B / 14 h / 23 °C

5.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 23 °C

6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

7.1: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 23 °C

With 1H-imidazole; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium aluminium tetrahydride; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja042733f

Reference yield:

(+)-(2R)-methyl-5-phenylpent-4-yn-1-ol (662168-58-3) → (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-(5R)-methyl-6-oxo-(1R)-propylhexyl ester (662168-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 20 h / 23 °C

2: 81 percent / Ni(cod)2; PBu₃; Et₃B / 14 h / 23 °C

3: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 24 h / 23 °C

4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

5: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 23 °C

With 1H-imidazole; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja042733f

upstream raw materials:

(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-hydroxy-(5R)-methyl-(1R)-propylhexyl ester

(-)-4-[(3S)-methyl-(5R)-(prop-2-ynyl)tetrahydrofuran-(2S)-yl]butan-1-ol

iodobenzene

1-bromo-3-phenylprop-2-yne

Downstream raw materials:

(+)-11,15-dibenzylidene-(14S)-(tert-butyldimethylsilanyloxy)-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxaicyclo[15.2.1]icosane-7-one

(-)-11,15-dibenzylidene-(14S)-hydroxy-(6S,13R,19R)-trimethyl-(9R)-propyl-8,20-dioxabicyclo[15.2.1]icosan-7-one