(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

Base Information

• Chemical Name: (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate
• CAS No.: 144070-33-7
• Molecular Formula: C₂₆H₃₇BrN₂O₉Si
• Molecular Weight: 629.577
• Mol file: 144070-33-7.mol

Synonyms:(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

Chemical Property of (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

There total 20 articles about (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate 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: 100.0%

(4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate (200055-61-4) → (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate (144070-33-7)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 23 ℃;

DOI:10.1021/jo00048a006

Reference yield: 42.0%

(4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3,3-dibromo-2-[N-(methoxycarbonyl)imino]pentanoate → (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate (144070-33-7) + (2E,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate (144001-89-8)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; water; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(97)01017-X

Reference yield:

(S)-2-[(1R,2S)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester (144001-85-4) → (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate (144070-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / KOt-Bu

2: 83 percent / N-bromosuccinimide / CH₂Cl₂ / 0.75 h / 24 °C

3: 100 percent / 1,4-diazabicyclo[2.2.2]octane

With 1,4-diaza-bicyclo[2.2.2]octane; N-Bromosuccinimide; potassium tert-butylate; In dichloromethane; 1: Wadsworth-Horner-Emmons olefination / 2: Bromination / 3: Isomerization;

DOI:10.1016/S0040-4020(97)01017-X

upstream raw materials:

(4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate

(S)-2-{(R)-2-Acetoxy-3,3-dibromo-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxycarbonyl-4-[(E)-methoxycarbonylimino]-butyl}-aziridine-1-carboxylic acid benzyl ester

(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

Methyl 2-(dimethoxyphosphinyl)-2-ethanoate