diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

Base Information

Chemical Name:diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate
CAS No.:740805-39-4
Molecular Formula:C₂₂H₃₄NO₇P
Molecular Weight:455.488
Hs Code.:

Synonyms:diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

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Chemical Property of diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

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Technology Process of diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

There total 14 articles about diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate 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: 76.0%

: diethyl (1'S,2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)-1'-(imidazole-1-thiocarbonyloxy)ethanephosphonate

: 740805-39-4
diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2.75h; Heating;
DOI:10.1002/ejoc.200500990

Reference yield:

: 682-30-4
Diethyl vinylphosphonate

: 740805-39-4
diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

Guidance literature:: Multi-step reaction with 5 steps

1: various solvent(s) / 16 h / 50 °C

2: 120 mg / HCl; water; H₂ / Pd/C / ethanol / 48 h / 40 °C

3: 52 percent / NaHCO₃ / ethanol / 8 h / 20 °C

4: 89 percent / tetrahydrofuran / 16 h / 20 °C

5: 76 percent / Bu₃SnH; azobis(isobutyronitrile) / toluene / 2.75 h / Heating

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;
DOI:10.1002/ejoc.200500990

Reference yield:

: 740805-26-9
(3S,4R,5S)-3,4-isopropylidenedioxy-5-methyl-1-pyrroline-N-oxide

: 740805-39-4
diethyl (2S,3S,4R,5S)-2'-(N-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidin-2-yl)ethanephosphonate

Guidance literature:: Multi-step reaction with 5 steps

1: various solvent(s) / 16 h / 50 °C

2: 120 mg / HCl; water; H₂ / Pd/C / ethanol / 48 h / 40 °C

3: 52 percent / NaHCO₃ / ethanol / 8 h / 20 °C

4: 89 percent / tetrahydrofuran / 16 h / 20 °C

5: 76 percent / Bu₃SnH; azobis(isobutyronitrile) / toluene / 2.75 h / Heating

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;
DOI:10.1002/ejoc.200500990