(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

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Chemical Name:(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester
CAS No.:850341-52-5
Molecular Formula:C₃₉H₅₂O₃
Molecular Weight:568.84
Hs Code.:

Synonyms:(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

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Chemical Property of (-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

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Technology Process of (-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

There total 11 articles about (-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl 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:

: (+)-trimethyl-[(3S)-methyl-6-phenylhexa-1,5-diynyl]silane

: 850341-52-5
(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 33 percent / Ni(cod)2; PBu₃; Et₃B / 20 °C

2: 52 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

3: 77 percent / CuI; Pd(PPh₃)4; pyrrolidine / 16 h / 20 °C

4: 84 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 14 h / 20 °C

With pyrrolidine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 3: Sonogashira coupling;
DOI:10.1021/ja042733f

Reference yield:

: 850341-50-3
(-)-4-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]butan-1-ol

: 850341-52-5
(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / imidazole; PPh₃; iodine / acetonitrile; diethyl ether / 4 h / 0 °C

2.1: LiCl; LDA / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C

2.2: tetrahydrofuran; hexane / 3 h / 0 °C

3.1: 191 mg / aq. NaOH / 2-methyl-propan-2-ol; methanol / 48 h / Heating

4.1: 84 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 14 h / 20 °C

With 1H-imidazole; sodium hydroxide; iodine; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja042733f

Reference yield:

: 850341-36-5
(-)-(5R)-allyl-(2S)-(4-iodobutyl)-(3S)-methyltetrahydrofuran

: 850341-52-5
(-)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5S)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiCl; LDA / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C

1.2: tetrahydrofuran; hexane / 3 h / 0 °C

2.1: 191 mg / aq. NaOH / 2-methyl-propan-2-ol; methanol / 48 h / Heating

3.1: 84 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 14 h / 20 °C

With sodium hydroxide; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja042733f