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

Base Information

• Chemical Name: benzyl (2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-4-(morpholin-4-yl)phenyl)carbamate
• CAS No.: 1341209-17-3
• Molecular Formula: C₂₈H₄₀N₂O₆Si
• Molecular Weight: 528.721

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

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

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

There total 6 articles about benzyl (2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-4-(morpholin-4-yl)phenyl)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: 92.0%

benzyl (2-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)-4-morpholinophenyl)carbamate (1341209-15-1) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl (2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-4-(morpholin-4-yl)phenyl)carbamate (1341209-17-3)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/jm200614t

Reference yield:

(2Z)-4-(5-bromo-2-nitrophenoxy)but-2-enyl propionate (911845-36-8) → benzyl (2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-4-(morpholin-4-yl)phenyl)carbamate (1341209-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium fluoride; potassium carbonate / N,N-dimethyl-formamide / 14 h / 120 °C / Molecular sieve

2: tin(II) chloride dihdyrate / ethanol / 18 h / Inert atmosphere; Reflux

3: pyridine / dichloromethane / 2 h / 20 °C

4: methanol; potassium hydroxide / tetrahydrofuran / 2 h / -5 - 20 °C

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

6: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; potassium fluoride; titanium acetate; tin(II) chloride dihdyrate; diethyl (2R,3R)-tartrate; potassium carbonate; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Sharpless epoxidation;

DOI:10.1021/jm200614t

Reference yield:

(Z)-4-(5-morpholino-2-nitrophenoxy)but-2-enyl propionate (1341209-09-3) → benzyl (2-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}-4-(morpholin-4-yl)phenyl)carbamate (1341209-17-3)

Guidance literature:

Multi-step reaction with 5 steps

1: tin(II) chloride dihdyrate / ethanol / 18 h / Inert atmosphere; Reflux

2: pyridine / dichloromethane / 2 h / 20 °C

3: methanol; potassium hydroxide / tetrahydrofuran / 2 h / -5 - 20 °C

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

5: 1H-imidazole; dmap / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; titanium acetate; tin(II) chloride dihdyrate; diethyl (2R,3R)-tartrate; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Sharpless epoxidation;

DOI:10.1021/jm200614t

upstream raw materials:

(2Z)-4-(5-bromo-2-nitrophenoxy)but-2-enyl propionate

(Z)-4-(5-morpholino-2-nitrophenoxy)but-2-enyl propionate

(Z)-4-(2-(benzyloxycarbonylamino)-5-morpholinophenoxy)but-2-enyl propionate

(Z)-benzyl (2-(4-hydroxybut-2-enyloxy)-4-morpholinophenyl)carbamate

Downstream raw materials:

[(3R,3aS)-7-morpholino-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl 3-nitrobenzene-1-sulfonate

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