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

Base Information

• Chemical Name: (4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate
• CAS No.: 200055-61-4
• Molecular Formula: C₂₆H₃₇BrN₂O₉Si
• Molecular Weight: 629.577
• Mol file: 200055-61-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate 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: 83.0%

(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate (144001-87-6) → (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)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 24 ℃; for 0.75h;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / KOt-Bu

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

With N-Bromosuccinimide; potassium tert-butylate; In dichloromethane; 1: Wadsworth-Horner-Emmons olefination / 2: Bromination;

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

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → (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)

Guidance literature:

Multi-step reaction with 12 steps

1: HCl / 24 h / Heating

2: CSA / dimethylformamide / 80 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

4: 73 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 1 h / 25 °C

5: 88 percent / iodine, Ph₃P, pyridine / toluene / 70 °C

6: 98 percent / pyridine, DMAP / CH₂Cl₂ / 24 °C

7: activated Zn, 95 percent EtOH / 1 h / 78 °C

8: NaBH₄ / tetrahydrofuran; H₂O / -43 °C

9: 85 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 12 h / 23 °C

10: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2.) 23 deg C

11: KO-t-Bu / CH₂Cl₂ / -78 to 24 deg C

12: N-bromosuccinimide / CH₂Cl₂ / 23 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; N-Bromosuccinimide; ammonium cerium(IV) nitrate; dimethylsulfide; ethanol; camphor-10-sulfonic acid; potassium tert-butylate; iodine; ozone; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00048a006

upstream raw materials:

(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

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

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

(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

(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