N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

Base Information

Chemical Name:N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide
CAS No.:153154-91-7
Molecular Formula:C₃₃H₃₆BrN₃O₇
Molecular Weight:666.569
Hs Code.:

Synonyms:N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

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Chemical Property of N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

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Technology Process of N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

There total 20 articles about N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide 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: 79.0%

: N-(2-Oxopropyl)-2-(N-benzoylamino)-3-bromo-4(S),5(S)-bis<(p-methoxybenzyl)oxy>-5--2(Z)-pentenamide

: 153154-91-7
N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

Guidance literature:: With trichloroacetic acid; In chloroform-d1; for 0.5h; Ambient temperature;
DOI:10.1021/jo00079a033

Reference yield:

: 85992-73-0
2-Benzoylamino-2-(diethoxyphosphoryl)essigsaeure-ethylester

: 153154-91-7
N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

2: aq. LiOH / tetrahydrofuran / 8 h / 50 °C

3: 1-hydroxybenzotriazole, DCC / CH₂Cl₂ / 2.17 h / Ambient temperature

4: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

5: Br₂ / CH₂Cl₂ / 0.01 h

6: DABCO / CH₂Cl₂ / 3 h / 0 °C

7: 79 percent / trichloroacetic acid / CDCl₃ / 0.5 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; oxalyl dichloride; bromine; benzotriazol-1-ol; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; trichloroacetic acid; In tetrahydrofuran; chloroform-d1; n-heptane; dichloromethane;
DOI:10.1021/jo00079a033

Reference yield:

: 137845-83-1
(2'S)-3--2(R),3(R)-bis<(p-methoxybenzyl)oxy>-1-propanal

: 153154-91-7
N-[(Z)-(3S,4R)-4-(S)-Aziridin-2-yl-2-bromo-3,4-bis-(4-methoxy-benzyloxy)-1-(2-oxo-propylcarbamoyl)-but-1-enyl]-benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

2: aq. LiOH / tetrahydrofuran / 8 h / 50 °C

3: 1-hydroxybenzotriazole, DCC / CH₂Cl₂ / 2.17 h / Ambient temperature

4: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

5: Br₂ / CH₂Cl₂ / 0.01 h

6: DABCO / CH₂Cl₂ / 3 h / 0 °C

7: 79 percent / trichloroacetic acid / CDCl₃ / 0.5 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; oxalyl dichloride; bromine; benzotriazol-1-ol; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; trichloroacetic acid; In tetrahydrofuran; chloroform-d1; n-heptane; dichloromethane;
DOI:10.1021/jo00079a033