(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

Base Information

Chemical Name:(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester
CAS No.:850341-55-8
Molecular Formula:C₃₁H₄₄O₅
Molecular Weight:496.687
Hs Code.:

Synonyms:(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

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Chemical Property of (-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

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Technology Process of (-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

There total 17 articles about (-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-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: 80.0%

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

: 850341-55-8
(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: (+)-6-[(5R)-allyl-(3S)-methyltetrahydrofuran-(2S)-yl]-(2S)-methylhexanoic acid 3-benzylidene-(5R)-methyl-7-phenyl-(1R)-propylhept-6-ynyl ester; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; for 3h;

With triphenylphosphine; In dichloromethane; for 0.666667h;
DOI:10.1021/ja042733f

Reference yield:

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

: 850341-55-8
(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 7 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

7.1: ozone / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂ / 3 h / -78 - 20 °C

7.3: 80 percent / PPh₃ / CH₂Cl₂ / 0.67 h

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; ozone; 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

: 850341-55-8
(-)-(2S)-methyl-6-[(3S)-methyl-(5R)-(2-oxoethyl)tetrahydrofuran-(2S)-yl]hexanoic acid (5R)-methyl-3-oxo-7-phenyl-(1R)-propylhept-6-ynyl ester

Guidance literature:: Multi-step reaction with 6 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

6.1: ozone / CH₂Cl₂ / -78 °C

6.2: Me₂S / CH₂Cl₂ / 3 h / -78 - 20 °C

6.3: 80 percent / PPh₃ / CH₂Cl₂ / 0.67 h

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; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 4.1: Sonogashira coupling;
DOI:10.1021/ja042733f