Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

Base Information

Chemical Name:Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester
CAS No.:453547-59-6
Molecular Formula:C₂₅H₃₀O₃Si
Molecular Weight:406.597
Hs Code.:

Synonyms:Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

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Chemical Property of Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

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Technology Process of Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

There total 5 articles about Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-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: 78.0%

: 453547-57-4
Benzoic acid (R)-1-((R)-1-(S)-oxiranyl-2-phenyl-ethyl)-allyl ester

: 1066-54-2
trimethylsilylacetylene

: 453547-59-6
Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

Benzoic acid (R)-1-((R)-1-(S)-oxiranyl-2-phenyl-ethyl)-allyl ester; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2005.08.116

Reference yield:

: 453547-53-0
Benzoic acid (1R,2S,3S)-2-benzyl-3,4-dihydroxy-1-vinyl-butyl ester

: 453547-59-6
Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / triethylamine; N,N-dimethylpyridin-4-amine / CH₂Cl₂ / 4 h / 20 °C

2.1: 86 percent / LiHMDS / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C

3.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 78 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2005.08.116

Reference yield:

: 453547-51-8
methyl 4-O-benzoyl-3-benzyl-6-bromo-3,6-dideoxy-α-D-altropyranoside

: 453547-59-6
Benzoic acid (1R,2S,3R)-2-benzyl-3-hydroxy-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / zinc; sodium cyanoborohydride / H₂O; propan-1-ol / 0.83 h / 95 °C

2.1: 82 percent / triethylamine; N,N-dimethylpyridin-4-amine / CH₂Cl₂ / 4 h / 20 °C

3.1: 86 percent / LiHMDS / tetrahydrofuran; hexane / 1.08 h / -78 - 20 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

4.2: 78 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

With dmap; n-butyllithium; sodium cyanoborohydride; triethylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; propan-1-ol; hexane; dichloromethane; water;
DOI:10.1016/j.tet.2005.08.116