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

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Chemical Name:(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-hydroxy-(5R)-methyl-(1R)-propylhexyl ester
CAS No.:662168-63-0
Molecular Formula:C₃₈H₅₂O₄
Molecular Weight:572.828
Hs Code.:

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

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

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

There total 13 articles about (+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-hydroxy-(5R)-methyl-(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: 97.0%

: 662168-62-9
(+)-(2S)-methyl-6-[(3S)-methyl-(5R)-(3-phenylprop-2-ynyl)tetrahydrofuran-(2S)-yl]hexanoic acid 3-benzylidene-6-(tert-butyldimethylsilanyloxy)-(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-6-hydroxy-(5R)-methyl-(1R)-propylhexyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;
DOI:10.1021/ja039716v DOI:10.1021/ja042733f

Reference yield:

: 1794-48-5
1-bromo-3-phenylprop-2-yne

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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium aluminium tetrahydride; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja042733f

Reference yield:

: 662168-57-2
(+)-(4S)-isopropyl-3-[(2R)-methyl-5-phenylpent-4-ynoyl]oxazolidin-2-one

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

Guidance literature:: Multi-step reaction with 5 steps

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

2: 96 percent / imidazole / dimethylformamide / 20 h / 23 °C

3: 81 percent / Ni(cod)2; PBu₃; Et₃B / 14 h / 23 °C

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

5: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h

With 1H-imidazole; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium aluminium tetrahydride; triethyl borane; tributylphosphine; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja042733f