(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Base Information

Chemical Name:(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester
CAS No.:208586-06-5
Molecular Formula:C₃₁H₅₂N₂O₆S₂Si
Molecular Weight:640.981
Hs Code.:

(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Synonyms:(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

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Chemical Property of (S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

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Technology Process of (S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

There total 15 articles about (S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic 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: 95.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 208585-91-5
(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

: 208586-06-5
(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4039(98)00518-8

Reference yield:

: 208585-79-9
(R)-4-(2-Methoxycarbonyl-2-methyl-propionyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

: 208586-06-5
(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 59 percent / NaBH₄ / ethanol / 20 °C

2: 5.54 g / NaH / tetrahydrofuran / 1.5 h / 20 °C

3: 4.87 g / NaOH / methanol; H₂O / Heating

4: tetrahydrofuran / 1.5 h / 20 °C

5: 4.40 g / tetrahydrofuran; dimethylformamide / 3 h / 20 °C

6: toluene / 72 h / Heating

7: 2.22 g / diethyl ether; methanol; hexane

8: 87 percent / K₂CO₃ / dimethylformamide / 2 h / 20 °C

9: DMAP / CH₂Cl₂ / 0.5 h / 20 °C

10: Cs₂CO₃ / methanol / 22 h / 20 °C

11: 878 mg / diethyl ether; methanol / 0 °C

12: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium hydride; potassium carbonate; caesium carbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Reduction / 2: Cyclization / 3: Hydrolysis / 4: Condensation / 5: Acylation / 6: Cyclization / 7: Esterification / 8: Alkylation / 9: Acylation / 10: Ring cleavage / 11: Methylation / 12: silylation;
DOI:10.1016/S0040-4020(99)00583-9

Reference yield:

: 208585-85-7
(S)-2-[2-((1S,7aR)-5,5-Dimethyl-3-oxo-dihydro-thiazolo[3,4-c]oxazol-1-yl)-2-methyl-propionylamino]-3-mercapto-2-methyl-propionic acid methyl ester

: 208586-06-5
(S)-2-[(2S,3R)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: toluene / 72 h / Heating

2: 2.22 g / diethyl ether; methanol; hexane

3: 87 percent / K₂CO₃ / dimethylformamide / 2 h / 20 °C

4: DMAP / CH₂Cl₂ / 0.5 h / 20 °C

5: Cs₂CO₃ / methanol / 22 h / 20 °C

6: 878 mg / diethyl ether; methanol / 0 °C

7: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; potassium carbonate; caesium carbonate; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: Esterification / 3: Alkylation / 4: Acylation / 5: Ring cleavage / 6: Methylation / 7: silylation;
DOI:10.1016/S0040-4020(99)00583-9