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

Base Information

Chemical Name:Benzoic acid (S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanylethynyl-pentyl ester
CAS No.:206998-30-3
Molecular Formula:C₂₃H₃₄O₄Si
Molecular Weight:402.606
Hs Code.:

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

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

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

There total 9 articles about Benzoic acid (S)-4-methyl-5-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanylethynyl-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: 82.0%

: 98-88-4
benzoyl chloride

: 206998-27-8
(S)-6-Methyl-7-(tetrahydro-pyran-2-yloxy)-1-trimethylsilanyl-hept-1-yn-3-ol

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1055/s-1998-5936

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

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

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / TSOH / diethyl ether / Ambient temperature

2: 94 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

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

4: NaH / tetrahydrofuran / 1.) r.t., 30 min, 2.) -78 deg C, 1.4 h; r.t., 1 h

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

6: 93 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

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

8: 96 percent / BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 1.5 h, 2.) -78 deg C, 50 min

9: 82 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate;
DOI:10.1055/s-1998-5936

Reference yield:

: 88588-59-4
(2S)-2-methyl-3-(tetrahydropyran-2-yloxy)propan-1-ol

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

Guidance literature:: Multi-step reaction with 7 steps

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

2: NaH / tetrahydrofuran / 1.) r.t., 30 min, 2.) -78 deg C, 1.4 h; r.t., 1 h

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

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

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

6: 96 percent / BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 1.5 h, 2.) -78 deg C, 50 min

7: 82 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / 0 °C

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