cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>

Base Information

• Chemical Name: cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>
• CAS No.: 86272-77-7
• Molecular Formula: C₃₀H₃₆N₄O₈Se
• Molecular Weight: 659.598
• Mol file: 86272-77-7.mol

Synonyms:

Chemical Property of cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>

There total 12 articles about cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl> 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: 72.0%

p-nitrophenyl selenocyanate (19188-18-2) + Cyclooxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl> (79816-29-8,79854-68-5,79854-69-6,79854-70-9) → cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl> (86272-77-7,86333-66-6)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00164a010

Reference yield:

benzyl prolinate hydrochloride (80089-24-3) → cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl> (86272-77-7,86333-66-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 46.5 percent / N-methylmorpholine, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂

2: 1.) H₂ / 1.) Pd/C / 1.) 1h; 2.) ethyl acetate/methanol, diethyl ether

3: 1.) m-dimethoxybenzene; 2.) di-tert-butyl dicarbonate, 1N KHCO₃ / 1.) trifluoroacetic acid, 0 deg C, 3h; 2.) dioxane

4: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

5: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

6: 1.)H₂; 2.) 1N KHCO₃ / 1.) Pd/C / 1.) acetic acid, 5h; 2.) dioxane, room temp.

7: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

8: 83 percent / 1N LiOH / dioxane

9: 90 percent / DCC / ethyl acetate / 1.) 0 deg C, 1h; 2.) room temp., 1h

10: 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; ethanol / 4 h

11: 72 percent / tributylphosphine / tetrahydrofuran / 2 h / Ambient temperature

With 4-methyl-morpholine; lithium hydroxide; tributylphosphine; di-tert-butyl dicarbonate; hydrogen; sodium cyanoborohydride; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; ethyl acetate;

DOI:10.1021/jo00164a010

Reference yield:

Methyl Ester of N-<3-<<3-<1-Oxo-2-(benzyloxycarbonyl)ethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-71-1) → cycloethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl> (86272-77-7,86333-66-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

2: 1.)H₂; 2.) 1N KHCO₃ / 1.) Pd/C / 1.) acetic acid, 5h; 2.) dioxane, room temp.

3: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

4: 83 percent / 1N LiOH / dioxane

5: 90 percent / DCC / ethyl acetate / 1.) 0 deg C, 1h; 2.) room temp., 1h

6: 4-pyrrolidinopyridine, H₂ / Pd/C / dioxane; ethanol / 4 h

7: 72 percent / tributylphosphine / tetrahydrofuran / 2 h / Ambient temperature

With lithium hydroxide; tributylphosphine; hydrogen; sodium cyanoborohydride; potassium hydrogencarbonate; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; water; acetic acid; ethyl acetate;

DOI:10.1021/jo00164a010

upstream raw materials:

p-nitrophenyl selenocyanate

Cyclooxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-prolyl>

benzyl prolinate hydrochloride

trans-N-(tert-Butoxycarbonyl)-3-<<3-(tert-butoxycarbonyl)-4-methoxyphenyl>oxy>proline

Downstream raw materials:

Zizyphine A