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

Base Information

• Chemical Name: Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester
• CAS No.: 478944-12-6
• Molecular Formula: C₁₉H₂₆O₃Si
• Molecular Weight: 330.499
• Mol file: 478944-12-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-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: 91.0%

trimethylsilylacetylene (1066-54-2) + Benzoic acid (R)-1-((R)-(S)-1-oxiranyl-ethyl)-allyl ester (478944-11-5) → Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester (478944-12-6)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0960-894X(02)00722-9

Reference yield:

Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester (79386-70-2) → Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester (478944-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Zn; NaBH₃CN / propan-1-ol; H₂O / 0.75 h / 95 °C

1.2: 75 percent / NaBH₄ / propan-1-ol; H₂O / 20 °C

2.1: TmCl; DMAP / CH₂Cl₂ / 0 - 20 °C

2.2: LiHMDS / tetrahydrofuran / -78 - 20 °C

3.1: 91 percent / BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

With dmap; n-butyllithium; boron trifluoride diethyl etherate; sodium cyanoborohydride; zinc; In tetrahydrofuran; propan-1-ol; dichloromethane; water;

DOI:10.1016/S0960-894X(02)00722-9

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (84170-91-2) → Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester (478944-12-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / NBS; BaCO₃ / CCl₄ / 0.58 h / Heating

2.1: Zn; NaBH₃CN / propan-1-ol; H₂O / 0.75 h / 95 °C

2.2: 75 percent / NaBH₄ / propan-1-ol; H₂O / 20 °C

3.1: TmCl; DMAP / CH₂Cl₂ / 0 - 20 °C

3.2: LiHMDS / tetrahydrofuran / -78 - 20 °C

4.1: 91 percent / BuLi; BF₃*Et₂O / tetrahydrofuran / -78 °C

With dmap; N-Bromosuccinimide; n-butyllithium; boron trifluoride diethyl etherate; sodium cyanoborohydride; barium carbonate; zinc; In tetrahydrofuran; propan-1-ol; tetrachloromethane; dichloromethane; water;

DOI:10.1016/S0960-894X(02)00722-9

upstream raw materials:

trimethylsilylacetylene

Benzoic acid (R)-1-((R)-(S)-1-oxiranyl-ethyl)-allyl ester

Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside