(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

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Chemical Name:(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
CAS No.:144001-89-8
Molecular Formula:C₂₆H₃₇BrN₂O₉Si
Molecular Weight:629.577
Hs Code.:
Mol file:144001-89-8.mol

(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

Synonyms:(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

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Chemical Property of (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 Edit

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Technology Process of (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

There total 18 articles about (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 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: 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

: 144070-33-7
(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

: 144001-89-8
(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

Guidance literature:: With sodium dithionite; In tetrahydrofuran; water; at 0 ℃; for 0.25h;
DOI:10.1016/S0040-4020(97)01017-X

Reference yield:

: 144001-85-4
(S)-2-[(1R,2S)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester

: 144001-89-8
(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

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: KOt-Bu / tetrahydrofuran / -20 °C

With N-Bromosuccinimide; potassium tert-butylate; In tetrahydrofuran; dichloromethane; 1: Wadsworth-Horner-Emmons olefination / 2: Bromination / 3: Isomerization;
DOI:10.1016/S0040-4020(97)01017-X