N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Base Information

• Chemical Name: N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester
• CAS No.: 104197-61-7
• Molecular Formula: C₆₄H₁₀₇N₇O₁₆Si
• Molecular Weight: 1258.68

Synonyms:N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Chemical Property of N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

There total 33 articles about N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester 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: 68.0%

Nα-linoleyl-Nδ-(tert-butoxycarbonyl)ornithine (104197-73-1) + C36H59N5O12Si → Nα-linoleyl-Nδ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester (104197-61-7)

Guidance literature:

With diethylphosphoryl cyanide; triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 38h;

DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester (104213-53-8) → Nα-linoleyl-Nδ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester (104197-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 10percent Pd-C / methanol / 32 h / 760 Torr / Ambient temperature

2: 68 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 38 h / 0 °C

With diethylphosphoryl cyanide; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

(2R,3S,4S)-5-benzyloxy-4-methyl-2,3-epoxypentanoic acid (106402-40-8) → Nα-linoleyl-Nδ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester (104197-61-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 72 percent / 28percent aq. NH₃ / 120 h / Ambient temperature

2: NEt₃ / dioxane; H₂O / 4 h / Ambient temperature

3: diethyl ether

4: 45.3 percent / H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

5: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

6: diethyl ether

7: pyridine / 8 h / Ambient temperature

8: 62 percent / NaH / tetrahydrofuran / 1.5 h / 0 °C

9: CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

10: diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 15 h / 0 °C

12: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

13: 100 percent / H₂ / 10percent Pd-C / methanol / 32 h / 760 Torr / Ambient temperature

14: 68 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 38 h / 0 °C

With pyridine; ammonium hydroxide; sodium hydroxide; diethylphosphoryl cyanide; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87959-X

upstream raw materials:

N^α-linoleyl-N^δ-(tert-butoxycarbonyl)ornithine

4-bromo-phenol

(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol

linoleic acid

Downstream raw materials:

echinocandin D

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