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

Base Information

Chemical Name: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
CAS No.:1341209-22-0
Molecular Formula:C₂₃H₂₅N₃O₆
Molecular Weight:439.468
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 95.0%

: 1341209-20-8
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

: 1341209-22-0
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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jm200614t

Reference yield:

: 911845-36-8
(2Z)-4-(5-bromo-2-nitrophenoxy)but-2-enyl propionate

: 1341209-22-0
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

Guidance literature:: Multi-step reaction with 8 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

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; potassium fluoride; n-butyllithium; titanium acetate; tin(II) chloride dihdyrate; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; potassium carbonate; potassium hydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Sharpless epoxidation;
DOI:10.1021/jm200614t

Reference yield:

: 1341209-16-2
benzyl 4-(4-(benzyloxycarbonylamino)-3-(((2R,3S)-3-(hydroxymethyl)oxiran-2-yl)methoxy)phenyl)piperazine-1-carboxylate

: 1341209-22-0
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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1021/jm200614t