benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

Base Information

• Chemical Name: benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate
• CAS No.: 1341209-20-8
• Molecular Formula: C₂₉H₃₉N₃O₆Si
• Molecular Weight: 553.731

Synonyms:benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

Chemical Property of benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

There total 7 articles about benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate 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: 65.0%

benzyl 4-(4-{[(benzyloxy)carbonyl]amino}-3-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}phenyl)piperazine-1-carboxylate (1341209-18-4) → benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate (1341209-20-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm200614t

Reference yield:

(2Z)-4-(5-bromo-2-nitrophenoxy)but-2-enyl propionate (911845-36-8) → benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate (1341209-20-8)

Guidance literature:

Multi-step reaction with 7 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

7: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

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

DOI:10.1021/jm200614t

Reference yield:

(Z)-4-(2-nitro-5-(piperazin-1-yl)phenoxy)but-2-enyl propionate (1341209-10-6) → benzyl 4-[(3R,3aS)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate (1341209-20-8)

Guidance literature:

Multi-step reaction with 6 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

6: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; n-butyllithium; titanium acetate; tin(II) chloride dihdyrate; diethyl (2R,3R)-tartrate; potassium hydroxide; In tetrahydrofuran; ethanol; hexane; 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

benzyl 4-(4-(benzyloxycarbonylamino)-3-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)piperazine-1-carboxylate

tert-butyldimethylsilyl chloride

benzyl 4-(4-{[(benzyloxy)carbonyl]amino}-3-{[(2R,3S)-3-{[(tert-butyldimethylsilyl)oxy]methyl}oxiran-2-yl]methoxy}phenyl)piperazine-1-carboxylate

Downstream raw materials:

benzyl 4-[(3R,3aS)-3-(hydroxymethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

benzyl 4-[(3R,3aS)-3-{[(3-nitrophenylsulfonyl)oxy]methyl}-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

benzyl 4-[(3S,3aS)-3-(acetamidomethyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl]piperazine-1-carboxylate

N-{[(3S,3aS)-7-[4-(3-nitrobenzyl)piperazin-1-yl]-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl]methyl}acetamide

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