4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

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Chemical Name:4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid
CAS No.:663919-04-8
Molecular Formula:C₆₇H₈₃N₃O₇S₂Si
Molecular Weight:1134.63
Hs Code.:

4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

Synonyms:4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

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Chemical Property of 4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

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Technology Process of 4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

There total 14 articles about 4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic 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: 71.0%

: 663919-03-7
4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid 2,2,2-trichloroethyl ester

: 663919-04-8
4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

Guidance literature:: With ammonium acetate; zinc; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/ja039258q

Reference yield:

: 180973-22-2
(2E)-5-[(triphenylmethyl)thio]-2-pentenal

: 663919-04-8
4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: TiCl₄; DIEA / CH₂Cl₂ / 2 h / -78 °C

1.2: 76 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 176 mg / DMAP / CH₂Cl₂ / 7 h / 20 °C

3.1: 71 percent / Zn; NH₄Ac / tetrahydrofuran / 5 h / 20 °C

With dmap; ammonium acetate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja039258q

Reference yield:

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

: 663919-04-8
4R-{2S-[2-(3S-hydroxy-7-tritylsulfanylhept-4E-enoylamino)propionylamino]-3-tritylsulfanylpropionylamino}-5R-methyl-3S-triisopropylsilanyloxyhexanoic acid

Guidance literature:: Multi-step reaction with 12 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

8.1: EtNH₂ / acetonitrile / 3 h / 20 °C

9.1: 174.1 mg / PyBOP; DIEA / CH₂Cl₂ / 2 h / 20 °C

10.1: EtNH₂ / acetonitrile / 5 h / 20 °C

11.1: 176 mg / DMAP / CH₂Cl₂ / 7 h / 20 °C

12.1: 71 percent / Zn; NH₄Ac / tetrahydrofuran / 5 h / 20 °C

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