Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester
• CAS No.: 84109-54-6
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557
• Mol file: 84109-54-6.mol

Synonyms:Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester

Chemical Property of Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester

There total 7 articles about Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl 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:

Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-oxo-1-vinyl-butyl ester → Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester (84109-54-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -35 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00341a052

Reference yield:

(2R,4aR,6S,7R,8S,8aS)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (84170-92-3) → Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester (84109-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 75 percent / NBS, BaCO₃ / CCl₄ / 1.5 h / 80 °C

3: Zn / propan-1-ol; H₂O / 0.5 h / 80 °C

4: NaBH₄ / ethanol / 0.5 h / -35 °C

With 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; barium carbonate; zinc; In propan-1-ol; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00341a052

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Benzoic acid (1R,2R,3R)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-2-methyl-1-vinyl-butyl ester (84109-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 75 percent / NBS, BaCO₃ / CCl₄ / 1.5 h / 80 °C

3: Zn / propan-1-ol; H₂O / 0.5 h / 80 °C

4: NaBH₄ / ethanol / 0.5 h / -35 °C

With 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; barium carbonate; zinc; In propan-1-ol; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja00341a052

upstream raw materials:

(2R,4aR,6S,7R,8S,8aS)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

tert-butyldimethylsilyl chloride

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

(2R,4aR,6S,8R,8aS)-6-Methoxy-8-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

Downstream raw materials:

Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-vinyl-butyl ester