tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:174787-39-4
Molecular Formula:C₂₅H₃₉N₃O₆SeSi
Molecular Weight:584.647
Hs Code.:

tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Property of tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

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Technology Process of tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

There total 8 articles about tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-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:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 174787-39-4
tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / NaH (60percent mineral oil) / tetrahydrofuran / 0 deg C, 1 h; RT, 2 h

2: hydrogen / 10percent Pd/C / ethanol

3: silica gel / Ambient temperature

4: 92 percent / NaI, NaHCO₃ / dimethylformamide / 15 h / Ambient temperature

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

6: NaI, N₂O₄ / diethyl ether; tetrahydrofuran / 26 h / 5 °C

7: sodium acetate / diethyl ether / 21 h / Ambient temperature

8: 1) 1.0M lithium bis(triethylsilyl)amide in THF / 1) -78 deg C, 5 min; 2) THF, -78 deg C to RT

With 2,6-dimethylpyridine; lithium bis(triethylsilyl)amide; hydrogen; sodium acetate; silica gel; dinitrogen tetraoxide; sodium hydride; sodium hydrogencarbonate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-95-S32

Reference yield:

: 174787-20-3
benzaldehyde N-(tert-butoxycarbonylmethyl)-N-((2R,3R)-2,3-epoxybutano)hydrazone

: 174787-39-4
tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: hydrogen / 10percent Pd/C / ethanol

2: silica gel / Ambient temperature

3: 92 percent / NaI, NaHCO₃ / dimethylformamide / 15 h / Ambient temperature

4: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

5: NaI, N₂O₄ / diethyl ether; tetrahydrofuran / 26 h / 5 °C

6: sodium acetate / diethyl ether / 21 h / Ambient temperature

7: 1) 1.0M lithium bis(triethylsilyl)amide in THF / 1) -78 deg C, 5 min; 2) THF, -78 deg C to RT

With 2,6-dimethylpyridine; lithium bis(triethylsilyl)amide; hydrogen; sodium acetate; silica gel; dinitrogen tetraoxide; sodium hydrogencarbonate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-95-S32

Reference yield:

: 174787-21-4
[N'-Benzyl-N-((2R,3R)-3-methyl-oxiranecarbonyl)-hydrazino]-acetic acid tert-butyl ester

: 174787-39-4
tert-butyl (2S,3R,5R,6S)-6-((R)-1-tert-butyldimethylsilyloxyethyl)-3-((R)-nitro(phenylseleno)methyl)-7-oxo-1,5-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: silica gel / Ambient temperature

2: 92 percent / NaI, NaHCO₃ / dimethylformamide / 15 h / Ambient temperature

3: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

4: NaI, N₂O₄ / diethyl ether; tetrahydrofuran / 26 h / 5 °C

5: sodium acetate / diethyl ether / 21 h / Ambient temperature

6: 1) 1.0M lithium bis(triethylsilyl)amide in THF / 1) -78 deg C, 5 min; 2) THF, -78 deg C to RT

With 2,6-dimethylpyridine; lithium bis(triethylsilyl)amide; sodium acetate; silica gel; dinitrogen tetraoxide; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.3987/COM-95-S32