(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Chemical Name:(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine
CAS No.:869857-99-8
Molecular Formula:C₂₃H₂₅N₃O₄
Molecular Weight:407.469
Hs Code.:

Synonyms:(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Chemical Property of (2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Technology Process of (2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

There total 10 articles about (2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine 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: 100.0%

: 869857-98-7
(3aS,4R,6S,6aR)-4-(2-Amino-phenylcarbamoyl)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester

: 869857-99-8
(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: With acetic acid; at 45 ℃; for 0.5h;
DOI:10.1039/b508855k

Reference yield:

: 1-{(4R,5S)-5-[(R)-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

: 869857-99-8
(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 10 steps

1: 74 percent / pyridine; DMAP

2: 55 percent / trimethylsilyl azide; tetrabutylammonium fluoride / dimethylformamide / 4.5 h / 90 °C

3: H₂ / Pd/C / methanol / 2 h / atmospheric pressure

4: 265 mg / DBU / methanol / 12 h / 20 °C

5: aq. NaHCO₃ / ethanol / 2 h / 20 °C

6: 0.966 g / aq. Zn(NO₃)2 / acetonitrile / 12 h / 50 °C

7: 92 percent / aq. NaIO₄ / tetrahydrofuran / 1 h / 20 °C

8: 82 percent / 2-methyl-2-butene; aq. NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol / 20 °C

9: 65 percent / PyBOP; diisopropylethylamine / 1 h / 20 °C

10: 100 percent / glac. AcOH / 0.5 h / 45 °C

With pyridine; dmap; sodium chlorite; zinc(II) nitrate; sodium periodate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilylazide; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b508855k

Reference yield:

: Methanesulfonic acid (R)-[(4R,5R)-5-(1-azido-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

: 869857-99-8
(2S,3S,4R,5S)-2-(1H-benzoimidazol-2-yl)-1-benzyloxycarbonyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd/C / methanol / 2 h / atmospheric pressure

2: 265 mg / DBU / methanol / 12 h / 20 °C

3: aq. NaHCO₃ / ethanol / 2 h / 20 °C

4: 0.966 g / aq. Zn(NO₃)2 / acetonitrile / 12 h / 50 °C

5: 92 percent / aq. NaIO₄ / tetrahydrofuran / 1 h / 20 °C

6: 82 percent / 2-methyl-2-butene; aq. NaClO₂; KH₂PO₄ / 2-methyl-propan-2-ol / 20 °C

7: 65 percent / PyBOP; diisopropylethylamine / 1 h / 20 °C

8: 100 percent / glac. AcOH / 0.5 h / 45 °C

With sodium chlorite; zinc(II) nitrate; sodium periodate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b508855k