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

Base Information

Chemical Name:(+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester
CAS No.:850341-51-4
Molecular Formula:C₃₉H₅₂O₃
Molecular Weight:568.84
Hs Code.:

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

There total 16 articles about (+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-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: 72.0%

: 850341-28-5
(S)-6-[(2S,3S,5S)-3-methyl-5-(prop-2-en-1-yl)tetrahydrofuran-2-yl]-2-methylhexanoic acid

: 850341-29-6
(+)-6-benzylidene-(8R)-methyl-10-phenyldec-9-yn-(4R)-ol

: 850341-51-4
(+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In dichloromethane; at 23 ℃; for 14h;
DOI:10.1021/ja042733f

Reference yield:

: 850341-44-5
(+)-(2R)-methyl-5-phenylpent-4-ynal

: 850341-51-4
(+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 69 percent / PPh₃ / CH₂Cl₂ / 16 h / 23 °C

2.1: MeLi / diethyl ether / 1.5 h / -78 °C

2.2: 92 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

3.1: 45 percent / Ni(cod)2; PBu₃; Et₃B / 14 h / 23 °C

4.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

5.1: 86 percent / Pd(PPh₃)4; CuI; pyrrolidine / 16 h / 20 °C

6.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 14 h / 23 °C

With pyrrolidine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 5.1: Sonogashira coupling;
DOI:10.1021/ja042733f

Reference yield:

: 850341-45-6
(+)-[6,6-tribromo-(4R)-methylhex-5-en-1-ynyl]benzene

: 850341-51-4
(+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: MeLi / diethyl ether / 1.5 h / -78 °C

1.2: 92 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 45 percent / Ni(cod)2; PBu₃; Et₃B / 14 h / 23 °C

3.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

4.1: 86 percent / Pd(PPh₃)4; CuI; pyrrolidine / 16 h / 20 °C

5.1: 72 percent / dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / CH₂Cl₂ / 14 h / 23 °C

With pyrrolidine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 4.1: Sonogashira coupling;
DOI:10.1021/ja042733f