benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

Base Information

Chemical Name:benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate
CAS No.:1341209-30-0
Molecular Formula:C₂₄H₃₁BrFNO₅Si
Molecular Weight:540.502
Hs Code.:

Synonyms:benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

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Chemical Property of benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

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Technology Process of benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

There total 6 articles about benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate 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: 96.8%

: 1341209-29-7
benzyl (4-bromo-5-fluoro-2-{[(2R,3S)-3-(hydroxymethyl)oxiran-2-yl]methoxy}phenyl)carbamate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1341209-30-0
benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;
DOI:10.1021/acsmedchemlett.7b00068

Reference yield:

: 1341209-27-5
(Z)-4-(5-bromo-4-fluoro-2-nitrophenoxy)but-2-en-1-ol

: 1341209-30-0
benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1: ammonium chloride; zinc / methanol / 24 h / 20 °C

2: sodium hydrogencarbonate / water; acetone / 0 - 20 °C

3: tert.-butylhydroperoxide; titanium acetate; diethyl (2R,3R)-tartrate / dichloromethane; toluene / 20 h / -40 °C / Molecular sieve

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; titanium acetate; diethyl (2R,3R)-tartrate; sodium hydrogencarbonate; ammonium chloride; zinc; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 3: Sharpless epoxidation;
DOI:10.1021/jm200614t

Reference yield:

: 1341209-28-6
benzyl (Z)-(4-bromo-5-fluoro-2-((4-hydroxybut-2-en-1-yl)oxy)phenyl)carbamate

: 1341209-30-0
benzyl (4-bromo-2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-5-fluorophenyl)carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: tert.-butylhydroperoxide; titanium acetate; diethyl (2R,3R)-tartrate / dichloromethane; toluene / 20 h / -40 °C / Molecular sieve

2: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; titanium acetate; diethyl (2R,3R)-tartrate; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Sharpless epoxidation;
DOI:10.1021/jm200614t