Technology Process of (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester
There total 15 articles about (E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl 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:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 5.55 g / Et3N / methanol / 1 h
2.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C
2.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C
3.1: H2 / PtO2 / CHCl3; methanol / 36 h / 2585.74 Torr
4.1: 4.2 g / Na2CO3 / CHCl3; methanol / 6 h / pH 7 / Heating
5.1: 91 percent / LiBH4 / CH2Cl2; tetrahydrofuran / 1.5 h / 23 °C
6.1: pyridine*SO3; DMSO; Et3N / CH2Cl2 / 2 h / 0 - 23 °C
7.1: 191 mg / CH2Cl2 / 2 h / 23 °C
8.1: TFA / CH2Cl2 / 1 h / 0 °C
9.1: HOBt; EDCI / CH2Cl2 / 0.17 h
9.2: 111 mg / DIPEA / CH2Cl2
With
lithium borohydride; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform;
7.1: Wittig reaction;
DOI:10.1021/jm050548m
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: Me3SiCl / 0 - 23 °C
2.1: 5.55 g / Et3N / methanol / 1 h
3.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C
3.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C
4.1: H2 / PtO2 / CHCl3; methanol / 36 h / 2585.74 Torr
5.1: 4.2 g / Na2CO3 / CHCl3; methanol / 6 h / pH 7 / Heating
6.1: 91 percent / LiBH4 / CH2Cl2; tetrahydrofuran / 1.5 h / 23 °C
7.1: pyridine*SO3; DMSO; Et3N / CH2Cl2 / 2 h / 0 - 23 °C
8.1: 191 mg / CH2Cl2 / 2 h / 23 °C
9.1: TFA / CH2Cl2 / 1 h / 0 °C
10.1: HOBt; EDCI / CH2Cl2 / 0.17 h
10.2: 111 mg / DIPEA / CH2Cl2
With
lithium borohydride; chloro-trimethyl-silane; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform;
8.1: Wittig reaction;
DOI:10.1021/jm050548m
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: LHMDS / hexane; tetrahydrofuran / 1 h / -78 °C
1.2: 79 percent / hexane; tetrahydrofuran / 2 h / -78 °C
2.1: H2 / PtO2 / CHCl3; methanol / 36 h / 2585.74 Torr
3.1: 4.2 g / Na2CO3 / CHCl3; methanol / 6 h / pH 7 / Heating
4.1: 91 percent / LiBH4 / CH2Cl2; tetrahydrofuran / 1.5 h / 23 °C
5.1: pyridine*SO3; DMSO; Et3N / CH2Cl2 / 2 h / 0 - 23 °C
6.1: 191 mg / CH2Cl2 / 2 h / 23 °C
7.1: TFA / CH2Cl2 / 1 h / 0 °C
8.1: HOBt; EDCI / CH2Cl2 / 0.17 h
8.2: 111 mg / DIPEA / CH2Cl2
With
lithium borohydride; hydrogen; sulfur trioxide pyridine complex; sodium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; chloroform;
6.1: Wittig reaction;
DOI:10.1021/jm050548m
