(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

Base Information

• Chemical Name: (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
• CAS No.: 869857-98-7
• Molecular Formula: C₂₃H₂₇N₃O₅
• Molecular Weight: 425.484
• Mol file: 869857-98-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 65.0%

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol (869857-96-5) + 1,2-diamino-benzene (95-54-5) → (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 (869857-98-7)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 1h;

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 → (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 (869857-98-7)

Guidance literature:

Multi-step reaction with 9 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

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; 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 → (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 (869857-98-7)

Guidance literature:

Multi-step reaction with 7 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

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; 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

upstream raw materials:

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol

1,2-diamino-benzene

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-formyl-5-methylpyrrolidine-3,4-diol

Downstream raw materials:

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