(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate

Base Information

• Chemical Name: (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate
• CAS No.: 1016652-32-6
• Molecular Formula: C₂₄H₃₃NO₃Si
• Molecular Weight: 411.616
• Mol file: 1016652-32-6.mol

Synonyms:(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate

Chemical Property of (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate

There total 2 articles about (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate 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: 97.0%

2-Picolinic acid (98-98-6) + (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-ol (1016652-27-9) → (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate (1016652-32-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol800300x

Reference yield:

2-Picolinic acid (98-98-6) + (S)-6-phenylhex-2-yne-1,4-diol (1016652-25-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate (1016652-32-6)

Guidance literature:

(S)-6-phenylhex-2-yne-1,4-diol; tert-butyldimethylsilyl chloride; With 1H-imidazole;

With Lindlar's catalyst; hydrogen;

2-Picolinic acid; With dmap; dicyclohexyl-carbodiimide;

DOI:10.1021/jo901728b

Reference yield: 98.0%

4,5-dihydro-4,4-dimethyl-2-phenoxazole (19312-06-2) + (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate (1016652-32-6) → (R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]-6-phenylhex-3-ene (1207609-74-2) + 4,5-dihydro-2-(4,5-dihydro-4,4-dimethyloxazol-2-yl)-4,4-dimethyl-oxazole (49585-66-2)

Guidance literature:

4,5-dihydro-4,4-dimethyl-2-phenoxazole; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

With copper(I) bromide dimethylsulfide complex; magnesium bromide; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-yl pyridine-2-carboxylate; In tetrahydrofuran; hexane; at 0 ℃; for 1h; regiospecific reaction;

DOI:10.1016/j.tet.2009.11.052

upstream raw materials:

2-Picolinic acid

(S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-ol

(S)-6-phenylhex-2-yne-1,4-diol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methylphenyl)-6-phenyl-3-hexene

(R,E)-1-[(tert-butyldimethylsilyl)oxy]-2-(2-methoxyphenyl)-6-phenyl-3-hexene

(R,E)-1-[(tert-butyldimethylsilyl)oxy]-2,6-diphenyl-3-hexene

(E)-1-[(tert-butyldimethylsilyl)oxy]-2,6-diphenyl-3-hexene