(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid

Base Information

Chemical Name:(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid
CAS No.:287967-62-8
Molecular Formula:C₂₅H₃₈N₂O₆S₂
Molecular Weight:526.719
Hs Code.:

(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid

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

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

There total 16 articles about (S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid 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:

: 249271-59-8
(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester

: 287967-62-8
(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid

Guidance literature:: With 4 A molecular sieve; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(99)00583-9

Reference yield:

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

: 287967-62-8
(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 14 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

13: 62 percent / NaH / dimethylformamide / 75 °C

14: tetrabutylammonium fluoride; 4A molecular sieves / tetrahydrofuran / 1.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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 / 13: Methylation / 14: desilylation; ester cleavage;
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

: 287967-62-8
(S)-2-[(2S,3R)-3-(tert-Butoxycarbonyl-methyl-amino)-2-hydroxy-4-(4-methoxy-benzylsulfanyl)-1,1-dimethyl-butyl]-4-methyl-4,5-dihydro-thiazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 9 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

8: 62 percent / NaH / dimethylformamide / 75 °C

9: tetrabutylammonium fluoride; 4A molecular sieves / tetrahydrofuran / 1.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; caesium carbonate; In tetrahydrofuran; 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 / 8: Methylation / 9: desilylation; ester cleavage;
DOI:10.1016/S0040-4020(99)00583-9