(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

Base Information

Chemical Name:(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester
CAS No.:334832-24-5
Molecular Formula:C₃₅H₄₁N₃O₈Si
Molecular Weight:659.811
Hs Code.:

(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

Synonyms:(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

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Chemical Property of (S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

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Technology Process of (S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

There total 11 articles about (S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid 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: 85.0%

: 334832-23-4
(S)-4-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methoxycarbonyl-ethylcarbamoyl]-5,2',2'-trimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester

: 334832-24-5
(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In chloroform; at 0 - 20 ℃; for 1.5h;
DOI:10.1246/cl.2001.102

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 334832-24-5
(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / KHCO₃ / dimethylformamide / 7 h / 0 - 20 °C

2: 100 percent / TsOH / acetone / 12 h / 20 °C

3: 100 percent / LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

4: DCC; HOBt / dimethylformamide / 7 h / 0 - 20 °C

5: TBAF / tetrahydrofuran / 6 h / 20 °C

6: Jones reagent / acetone / 3 h / 0 - 20 °C

7: I₂; PPh₃; Et₃N / CHCl₃ / 0.5 h / 0 °C

8: LiOH / methanol

9: diphenylphosphoryl azide; Et₃N / dimethylformamide / 7 h / 0 - 20 °C

10: 85 percent / TFA / CHCl₃ / 1.5 h / 0 - 20 °C

With lithium hydroxide; jones reagent; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; iodine; benzotriazol-1-ol; potassium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; water; N,N-dimethyl-formamide; acetone; 6: Jones oxidation;
DOI:10.1246/cl.2001.102

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 334832-24-5
(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / TsOH / acetone / 12 h / 20 °C

2: 100 percent / LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

3: DCC; HOBt / dimethylformamide / 7 h / 0 - 20 °C

4: TBAF / tetrahydrofuran / 6 h / 20 °C

5: Jones reagent / acetone / 3 h / 0 - 20 °C

6: I₂; PPh₃; Et₃N / CHCl₃ / 0.5 h / 0 °C

7: LiOH / methanol

8: diphenylphosphoryl azide; Et₃N / dimethylformamide / 7 h / 0 - 20 °C

9: 85 percent / TFA / CHCl₃ / 1.5 h / 0 - 20 °C

With lithium hydroxide; jones reagent; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; iodine; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform; water; N,N-dimethyl-formamide; acetone; 5: Jones oxidation;
DOI:10.1246/cl.2001.102