{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

Base Information

Chemical Name:{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester
CAS No.:794525-88-5
Molecular Formula:C₅₄H₇₄N₄O₈Si
Molecular Weight:935.289
Hs Code.:

{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

Synonyms:{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

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Chemical Property of {1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

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Technology Process of {1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

There total 14 articles about {1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl 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: 88.0%

: 74214-38-3
L-leucyl-L-phenylalaninamide hydrochloride

: 794525-87-4
5(S)-tert-butoxycarbonylamino-4(R)-(tert-butyldimethylsilanyloxy)-6-phenyl-2-(4-(2-phenyl-1,3-dioxolan-2-yl)-benzyl)hexanoic acid

: 794525-88-5
{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jo0486948

Reference yield:

: 90-90-4
(4-bromophenyl)(phenyl)methanone

: 794525-88-5
{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / p-TsOH / benzene / 44 h / Heating

2.1: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 0.5 h / -78 °C

3.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

4.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

5.1: LiOH / dimethylformamide; H₂O / 20 °C

6.1: imidazole / dimethylformamide / 20 °C

6.2: MeOH / dimethylformamide / 2 h

7.1: 88 percent / 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Hunig's base / dimethylformamide / 20 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo0486948

Reference yield:

: 51987-73-6
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

: 794525-88-5
{1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-[1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3-(1S)-methyl-butylcarbamoyl]-5-[4-(2-phenyl-[1.3]dioxolan-2-yl)phenyl]-pentyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.1: 7.8 g / NaBH₄ / toluene; ethanol / 8 h / -78 - 0 °C

3.1: 89 percent / KOH / ethanol / 2 h / 20 °C

4.1: 90 percent / EtONa / ethanol / 20 °C

5.1: LiOH / dimethylformamide; H₂O / 6 h / 50 °C

6.1: toluene / 5 h / Heating

7.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

7.2: tetrahydrofuran / 0.5 h / -78 °C

7.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

8.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

9.1: LiOH / dimethylformamide; H₂O / 20 °C

10.1: imidazole / dimethylformamide / 20 °C

10.2: MeOH / dimethylformamide / 2 h

11.1: 88 percent / 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Hunig's base / dimethylformamide / 20 °C

With 1H-imidazole; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; hydrogen; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0486948