(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

Chemical Name:(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
CAS No.:161692-28-0
Molecular Formula:C₃₂H₃₅N₂O₁₀PSi
Molecular Weight:666.697
Hs Code.:

Synonyms:(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Chemical Property of (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Technology Process of (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 10 articles about (4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-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:

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

: 161692-28-0
(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / K₂CO₃ / acetone / 4 h / Heating

2: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h

5: CH₂Cl₂ / 1 h

6: 86 percent / anisole, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

7: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C

8: 98 percent / Et₃N / toluene / 5 h / Ambient temperature

9: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzyl bromide; titanium tetrachloride; sodium hydride; potassium carbonate; methoxybenzene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1248/cpb.42.1381

Reference yield:

: 96035-98-2
(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone

: 161692-28-0
(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / NaH / tetrahydrofuran / 2 h / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h

4: CH₂Cl₂ / 1 h

5: 86 percent / anisole, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

6: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C

7: 98 percent / Et₃N / toluene / 5 h / Ambient temperature

8: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzyl bromide; titanium tetrachloride; sodium hydride; methoxybenzene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.42.1381

Reference yield:

: 105318-04-5
(3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone

: 161692-28-0
(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

2: Et₃N / CH₂Cl₂ / 1 h

3: CH₂Cl₂ / 1 h

4: 86 percent / anisole, TiCl₄ / CH₂Cl₂ / 1 h / 0 °C

5: 93 percent / γ-collidine / dimethylformamide / 1.5 h / 65 °C

6: 98 percent / Et₃N / toluene / 5 h / Ambient temperature

7: 1.) NaH, 2.) benzyl bromide / 1.) THF, toluene, -20 deg C, 1 h, 2.) THF, toluene, -20 deg C, 2 h

With 2,4,6-trimethyl-pyridine; hydrogen; benzyl bromide; titanium tetrachloride; sodium hydride; methoxybenzene; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.42.1381