methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

Base Information

Chemical Name:methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate
CAS No.:478937-55-2
Molecular Formula:C₃₄H₄₀N₄O₅S₃Si
Molecular Weight:708.999
Hs Code.:

Synonyms:methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

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Chemical Property of methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

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Technology Process of methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

There total 15 articles about methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate 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: 97.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 478937-53-0
methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-hydroxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

: 478937-55-2
methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

Guidance literature:: With 1H-imidazole; In chloroform; at 0 ℃; for 12h;
DOI:10.1246/bcsj.75.1583

Reference yield:

: 478937-37-0
(S)-2-(3-t-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-1,3-thiazole-4-carboxamide

: 478937-55-2
methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 70 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 10 h / 20 °C

2: KHCO₃ / 1,2-dimethoxy-ethane / 2 h / 0 °C

3: 1.03 g / TFAA; pyridine / 1,2-dimethoxy-ethane / 1 h / 0 °C

4: 98 percent / 1M LiOH / H₂O; dioxane / 3.5 h / 0 - 20 °C

5: 98 percent / Et₃N; DPPA / dimethylformamide / 9.5 h / 0 - 20 °C

6: 82 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 16 h / 50 °C

7: 66 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

8: 72 percent / DEAD; Ph₃P / tetrahydrofuran / 1 h / 0 °C

9: 70 percent / TFA / CHCl₃ / 2 h / 20 °C

10: 97 percent / imidazole / CHCl₃ / 12 h / 0 °C

With Lawessons reagent; pyridine; 1H-imidazole; lithium hydroxide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; chloroform; water; N,N-dimethyl-formamide; 8: Mitsunobu reaction;
DOI:10.1246/bcsj.75.1583

Reference yield:

: 4-(2-ethoxycarbonyl-2-oxo-ethylthiocarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 478937-55-2
methyl (S)-2-{2-[2-(1-t-butoxycarbonylamino-2-t-butyldiphenylsiloxyethyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,3-thiazole-4-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 647 mg / TFAA; pyridine / 1,2-dimethoxy-ethane / 1 h / 0 °C

2.1: 97 percent / 1M LiOH / H₂O; dioxane / 3.5 h / 0 - 20 °C

3.1: ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 0 °C

3.2: 99 percent / 28 percent aq. NH₃ / tetrahydrofuran / 0.08 h / 0 °C

4.1: 70 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 10 h / 20 °C

5.1: KHCO₃ / 1,2-dimethoxy-ethane / 2 h / 0 °C

6.1: 1.03 g / TFAA; pyridine / 1,2-dimethoxy-ethane / 1 h / 0 °C

7.1: 98 percent / 1M LiOH / H₂O; dioxane / 3.5 h / 0 - 20 °C

8.1: 98 percent / Et₃N; DPPA / dimethylformamide / 9.5 h / 0 - 20 °C

9.1: 82 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 16 h / 50 °C

10.1: 66 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

11.1: 72 percent / DEAD; Ph₃P / tetrahydrofuran / 1 h / 0 °C

12.1: 70 percent / TFA / CHCl₃ / 2 h / 20 °C

13.1: 97 percent / imidazole / CHCl₃ / 12 h / 0 °C

With Lawessons reagent; pyridine; 1H-imidazole; lithium hydroxide; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; chloroform; water; N,N-dimethyl-formamide; 11.1: Mitsunobu reaction;
DOI:10.1246/bcsj.75.1583