(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

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Chemical Name:(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one
CAS No.:214837-31-7
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

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Chemical Property of (1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

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Technology Process of (1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

There total 4 articles about (1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one 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: 87.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 145574-39-6
benzyl (1S,4S,5S)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 214837-31-7
(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/S0960-894X(01)00495-4

Reference yield:

: 145574-13-6
benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 214837-31-7
(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / K₂S₂O₈; aq. NaHCO₃ / acetonitrile / 5 h / 80 °C / pH 4.5

2: 87 percent / TsOH / tetrahydrofuran / 12 h / 20 °C

With dipotassium peroxodisulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0960-894X(01)00495-4

Reference yield:

: [(2S,3S)-2-((R)-1,2-Dihydroxy-ethyl)-1-(3,4-dimethoxy-benzyl)-4-oxo-azetidin-3-yl]-carbamic acid benzyl ester

: 214837-31-7
(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / tetrahydrofuran / 4 h / Heating

2: 86 percent / Bu₄NBr / dimethylformamide / 5 h / 140 °C

3: 40 percent / K₂S₂O₈, NaHCO₃ / acetonitrile; H₂O / 100 °C / pH 4.5

4: 76 percent / p-toluenesulfonic acid / dimethylformamide / 24 h

With dipotassium peroxodisulfate; tetrabutylammomium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm980023c