1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6S,6aR)-6-(bromomethyl)-5-(1,1-dimethylethoxy)carbonyltetrahydro-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,6S,6aR)-6-(bromomethyl)-5-(1,1-dimethylethoxy)carbonyltetrahydro-2,2-dimethyl-4H-1,3-dioxolo4,5-cpyrrol-4-yl-, 2-ethyl 1-(phenylmethyl) ester
CAS No.:222631-38-1
Molecular Formula:C28H36 Br N3 O8
Molecular Weight:622.5
Hs Code.:

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

Chemical Property:

PSA：131.55000
LogP:5.52640

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

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

There total 12 articles about 1H-Pyrrole-1,2-dicarboxylic acid, 3-amino-4-(3aS,4S,6S,6aR)-6-(bromomethyl)-5-(1,1-dimethylethoxy)carbonyltetrahydro-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:

: 124-63-0
methanesulfonyl chloride

: 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

: 222631-38-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-5-bromo-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: With dmap; tetrabutylammomium bromide; triethylamine; In dichloromethane; toluene;

Reference yield:

: 3-Amino-4-((3aS,4S,6R,6aR)-5-tert-butoxycarbonyl-6-methanesulfonyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

: 222631-38-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-5-bromo-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: With tetrabutylammomium bromide; In toluene; at 100 ℃; for 2h;
DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

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

: 222631-38-1
(1S)-1-(3-amino-N-benzyloxycarbonyl-2-ethoxycarbonylpyrrol-4-yl)-5-bromo-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

Guidance literature:: Multi-step reaction with 8 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

7: Et₃N; DMAP / CH₂Cl₂ / 1 h

8: 0.277 g / Bu₄NBr / toluene / 2 h / 100 °C

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