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 amide

Base Information

Chemical Name: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 amide
CAS No.:106391-79-1
Molecular Formula:C₄₃H₆₄N₆O₁₃Si
Molecular Weight:901.099
Hs Code.:

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 amide

Synonyms: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 amide

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Chemical Property of 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 amide

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Technology Process of 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 amide

There total 35 articles about 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 amide 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: 38.0%

: 104213-53-8
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

: 106391-79-1
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 amide

Guidance literature:: With ammonia; In methanol; for 132h; Ambient temperature;
DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

: 104241-22-7
(2S,3S,4S)-2-amino-3-hydroxy-4-methyl-5-benzyloxypentanoic acid

: 106391-79-1
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 amide

Guidance literature:: Multi-step reaction with 12 steps

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

2: diethyl ether

3: 45.3 percent / H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

4: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

5: diethyl ether

6: pyridine / 8 h / Ambient temperature

7: 62 percent / NaH / tetrahydrofuran / 1.5 h / 0 °C

8: CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

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

11: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

12: 38 percent / NH₃(g) / methanol / 132 h / Ambient temperature

With pyridine; sodium hydroxide; diethylphosphoryl cyanide; ammonia; 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

Reference yield:

: 81520-04-9
(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol

: 106391-79-1
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 amide

Guidance literature:: Multi-step reaction with 14 steps

1: 79 percent / pyridinium dichromate / dimethylformamide / 45 h / Ambient temperature

2: 72 percent / 28percent aq. NH₃ / 120 h / Ambient temperature

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

4: diethyl ether

5: 45.3 percent / H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

6: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

7: diethyl ether

8: pyridine / 8 h / Ambient temperature

9: 62 percent / NaH / tetrahydrofuran / 1.5 h / 0 °C

10: CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

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

13: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

14: 38 percent / NH₃(g) / methanol / 132 h / Ambient temperature

With pyridine; ammonium hydroxide; sodium hydroxide; dipyridinium dichromate; diethylphosphoryl cyanide; ammonia; 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