4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

Base Information

Chemical Name:4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester
CAS No.:663919-01-5
Molecular Formula:C₅₅H₆₅Cl₃N₂O₆SSi
Molecular Weight:1016.64
Hs Code.:

4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

Synonyms:4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

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Chemical Property of 4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

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Technology Process of 4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

There total 8 articles about 4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl 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: 93.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 663919-00-4
4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-3S-hydroxy-5-methylhexanoic acid 2,2,2-trichloroethyl ester

: 663919-01-5
4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 4.5h;
DOI:10.1021/ja039258q

Reference yield:

: 22838-58-0
Boc-D-Val-OH

: 663919-01-5
4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: EDAC*HCl; DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

2.1: LDA / tetrahydrofuran / 1 h / -78 °C

2.2: 2.38 g / tetrahydrofuran / 0.75 h / -78 °C

3.1: 70 percent / potassium borohydride / methanol / 0.83 h / -78 - 0 °C

4.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

5.1: 569 g / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

6.1: TFA / CH₂Cl₂ / 3 h / 0 °C

7.1: 808.5 mg / PyBOP; DIEA / 0.33 h / 20 °C

8.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; potassium borohydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 2.2: Claisen condensation;
DOI:10.1021/ja039258q

Reference yield:

: 182360-34-5
D-N-(tert-butoxycarbonyl)valine pentafluorophenyl ester

: 663919-01-5
4R-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3S-tritylsulfanylpropionylamino]-5-methyl-3-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 2.38 g / tetrahydrofuran / 0.75 h / -78 °C

2.1: 70 percent / potassium borohydride / methanol / 0.83 h / -78 - 0 °C

3.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

4.1: 569 g / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

5.1: TFA / CH₂Cl₂ / 3 h / 0 °C

6.1: 808.5 mg / PyBOP; DIEA / 0.33 h / 20 °C

7.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; potassium borohydride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1.2: Claisen condensation;
DOI:10.1021/ja039258q