ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate

Base Information

• Chemical Name: ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate
• CAS No.: 244057-93-0
• Molecular Formula: C₂₉H₃₈O₃Si
• Molecular Weight: 462.704
• Mol file: 244057-93-0.mol

Synonyms:ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate

Chemical Property of ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate

There total 1 articles about ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate 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: 85.0%

Triethyl orthoacetate (78-39-7) + 8-(tert-butyl-diphenyl-silanyloxy)-2-methyl-oct-2-en-6-yn-1-ol (213328-01-9) → ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate (244057-93-0)

Guidance literature:

With propionic acid; for 16h; Heating;

DOI:10.1021/jo990376z

Reference yield: 88.0%

acetic acid tert-butyl ester (540-88-5) + ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate (244057-93-0) → tert-butyl 10-(tert-butyldiphenylsilyloxy)-5-isopropenyl-3-oxo-8-decynoate (244057-95-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature;

DOI:10.1021/jo990376z

Reference yield:

ethyl 8-(tert-butyldiphenylsilyloxy)-5-isopropenyl-6-octynoate (244057-93-0) → 2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-acetoxy-2-methyl-2-propenyl)furan (244058-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / LiN(TMS)2 / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature

2: 2.) PPTS / 1.) room temperature, 96 h, 2.) EtOH, 80 deg C, 35 min

3: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 96 percent / tetrahydrofuran

5: 94 percent / DMAP / pyridine / 1 h / Ambient temperature

With dmap; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo990376z

upstream raw materials:

Triethyl orthoacetate

8-(tert-butyl-diphenyl-silanyloxy)-2-methyl-oct-2-en-6-yn-1-ol

Downstream raw materials:

tert-butyl 10-(tert-butyldiphenylsilyloxy)-5-isopropenyl-3-oxo-8-decynoate

2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-formylfuran

2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(hydroxymethyl)furan

2-<2-isopropenyl-7-(tert-butyldimethylsilyloxy)-5-heptynyl>-3-carbo-tert-butoxy-5-(1-hydroxy-2-methyl-2-propenyl)furan