1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester

Base Information

Chemical Name:1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester
CAS No.:284490-17-1
Molecular Formula:C₂₈H₃₇N₃O₉
Molecular Weight:559.616
Hs Code.:
Mol file:284490-17-1.mol

1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester

Synonyms:1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester

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Chemical Property of 1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester

Chemical Property:

PSA：151.78000
LogP:4.12380

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

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Technology Process of 1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester

There total 9 articles about 1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6R,6aR)-5-(1,1-dimethylethoxy)carbonyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) 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:

: 222631-12-1
1-benzyl 2-ethyl 3-amino-4-((3aS,4S,6R,6aR)-5-(tert-butoxycarbonyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo [4,5-c]pyrrol-4-yl)-1H-pyrrole-1,2-dicarboxylate

: 284490-17-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 284490-17-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

2: dimethylformamide / 1 h / 65 - 70 °C

3: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

4: 3.46 g / NaOAc / methanol / 16 h / 20 °C

5: 3.68 g / DBU / CH₂Cl₂ / 4 h / Heating

6: TBAF / tetrahydrofuran / 1 h

With tetrabutyl ammonium fluoride; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Condensation / 3: Hydrolysis / 4: Condensation / 5: Substitution / 6: Substitution;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

: 153172-31-7
(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

: 284490-17-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 8 steps

1.1: NCS / pentane / 1 h

1.2: LiTMP / tetrahydrofuran / -78 °C

2.1: 0.83 g / tetrahydrofuran / 1 h / -78 °C

3.1: 85 percent / CH₂Cl₂ / 16 h / 20 °C

4.1: dimethylformamide / 1 h / 65 - 70 °C

5.1: 0.68 g / aq. AcOH / tetrahydrofuran / 1.5 h / 20 °C

6.1: 3.46 g / NaOAc / methanol / 16 h / 20 °C

7.1: 3.68 g / DBU / CH₂Cl₂ / 4 h / Heating

8.1: TBAF / tetrahydrofuran / 1 h

With N-chloro-succinimide; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; pentane; 1.1: Chlorination / 1.2: Elimination / 2.1: Addition / 3.1: Substitution / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Condensation / 7.1: Substitution / 8.1: Substitution;
DOI:10.1016/S0040-4020(00)00194-0