(1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate

Base Information

• Chemical Name: (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate
• CAS No.: 318234-74-1
• Molecular Formula: C₃₆H₅₂O₅Si
• Molecular Weight: 592.891
• Mol file: 318234-74-1.mol

Synonyms:(1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate

Chemical Property of (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate

There total 7 articles about (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate 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: 88.0%

(2R,3R,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-[(E,3S)-3-hydroxy-1-octenyl]cyclopentan-1-one (276241-82-8) + 2-(4-hexynyloxy)benzoic acid (318234-73-0) → (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate (318234-74-1)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1021/ja003119g

Reference yield:

6-bromo-2-hexyne (55402-12-5) → (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate (318234-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH; I₂; imidazole / dimethylformamide; various solvent(s) / 1 h / 0 - 20 °C

1.2: 73 percent / dimethylformamide; various solvent(s) / 24 h / 50 °C

2.1: 0.768 g / KOH; water / 16 h / 20 °C

3.1: 88 percent / diisopropyl carbodiimide; DMAP / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; water; iodine; sodium hydride; diisopropyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja003119g

Reference yield:

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (61305-35-9) → (1S,2E)-3-[(1R,2R,5R)-5-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-oxocyclopentyl]-1-pentyl-2-propenyl 2-(4-hexynyloxy)benzoate (318234-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.2368 g / aq. AcOH / tetrahydrofuran / 9 h / 20 °C

2: 88 percent / diisopropyl carbodiimide; DMAP / CH₂Cl₂ / 20 °C

With dmap; acetic acid; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja003119g

upstream raw materials:

(2R,3R,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-2-(2-butynyl)-3-[(E,3S)-3-hydroxy-1-octenyl]cyclopentan-1-one

2-(4-hexynyloxy)benzoic acid

6-bromo-2-hexyne

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone