Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Base Information

• Chemical Name: Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline
• CAS No.: 86272-74-4
• Molecular Formula: C₃₃H₄₃N₃O₁₀
• Molecular Weight: 641.719
• Mol file: 86272-74-4.mol

Synonyms:

Chemical Property of Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

There total 8 articles about Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline 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: 98.0%

Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-oxoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-73-3) → Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-74-4,86333-64-4)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; acetic acid;

DOI:10.1021/jo00164a010

Reference yield:

benzyl prolinate hydrochloride (80089-24-3) → Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-74-4,86333-64-4)

Guidance literature:

Multi-step reaction with 7 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

With 4-methyl-morpholine; di-tert-butyl dicarbonate; hydrogen; sodium cyanoborohydride; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1'-carbonyldiimidazole; 1,3-Dimethoxybenzene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetic acid;

DOI:10.1021/jo00164a010

Reference yield:

Methyl Ester of N-<3-<<3-Carboxy-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-70-0) → Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline (86272-74-4,86333-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / N,N-carbonyldiimidazole / tetrahydrofuran / 5 h / 50 °C

2: 88 percent / NaNO₂ / acetic acid; H₂O / 0 °C

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

4: 98 percent / NaCNBH₃ / tetrahydrofuran; acetic acid

With hydrogen; sodium cyanoborohydride; potassium hydrogencarbonate; 1,1'-carbonyldiimidazole; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/jo00164a010

upstream raw materials:

Methyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-oxoethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

benzyl prolinate hydrochloride

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

Methyl Ester of N-<3-<<3-(tert-Butoxycarbonyl)-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Downstream raw materials:

N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

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

Pentafluorophenyl Ester of N-<3-<<3-<2-(Carbobenzoxyamino)-1-hydroxyethyl>-4-methoxyphenyl>oxy>-N-(tert-butoxycarbonyl)-(2S,3S)-prolyl>-(S)-proline

Zizyphine A