Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

Base Information

Chemical Name:Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester
CAS No.:206998-29-0
Molecular Formula:C₂₀H₂₆O₄
Molecular Weight:330.424
Hs Code.:

Synonyms:Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

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Chemical Property of Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

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Technology Process of Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

There total 11 articles about Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl 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: 96.0%

: 98-88-4
benzoyl chloride

: 206998-28-9
(S)-6-Methyl-7-(tetrahydro-pyran-2-yloxy)-hept-1-yn-3-ol

: 206998-29-0
Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 12h;
DOI:10.1055/s-1998-5936

Reference yield: 47.0%

: 206998-30-3
Benzoic acid (S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanylethynyl-pentyl ester

: 206998-29-0
Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1055/s-1998-5936

Reference yield:

: 206998-23-4
(E)-(S)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-pent-2-enoic acid methyl ester

: 206998-29-0
Benzoic acid (S)-1-ethynyl-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / 5percent Pd/C / ethyl acetate / 1 h / Ambient temperature

2: 93 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -55 deg C, 1 h, 2.) CH₂Cl₂, 5 min

4: 96 percent / BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 1.5 h, 2.) -78 deg C, 50 min

5: 82 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / 0 °C

6: 47 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate;
DOI:10.1055/s-1998-5936