5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

Base Information

• Chemical Name: 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-
• CAS No.: 222631-11-0
• Molecular Formula: C26H45 N3 O7 Si
• Molecular Weight: 539.745

Synonyms:5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

Chemical Property of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

Chemical Property:

• PSA: 119.35000
• LogP: 4.40518

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)-

There total 19 articles about 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-1-cyano-2-(2-ethoxy-2-oxoethyl)aminoethenyl-6-(1,1-dimethylethyl)dimethylsilyloxymethyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aS,4S,6R,6aR)- 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:

(3aR,4R,6S,6aS)-tert-butyl 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-((E/Z)-1-cyano-2-hydroxyvinyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate (222631-10-9) + glycine ethyl ester hydrochloride (623-33-6) → N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol (222631-11-0)

Guidance literature:

With sodium acetate; In methanol; at 20 ℃; for 16h;

Reference yield:

glycine ethyl ester hydrochloride (623-33-6) + (1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol (284490-14-8) → N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol (222631-11-0)

Guidance literature:

With sodium acetate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/S0040-4020(00)00194-0

Reference yield:

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole (153172-31-7) → N-tert-butoxycarbonyl-7-O-tert-butyldimethylsilyl-2-cyano-1,2,3,6-tetradeoxy-1-N-(ethoxycarbonylmethylamino)-3,6-imino-4,5-O-isopropylidene-D-allo-hept-1-enitol (222631-11-0)

Guidance literature:

Multi-step reaction with 6 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

With N-chloro-succinimide; sodium acetate; acetic acid; 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;

DOI:10.1016/S0040-4020(00)00194-0

upstream raw materials:

glycine ethyl ester hydrochloride

(1S)-N-tert-butoxycarbonyl-5-O-tert-butyldimethylsilyl-1-C-(1-cyano-2-hydroxyethenyl)-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

di-tert-butyl dicarbonate

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

Downstream raw materials:

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

(3aS,4S,6R,6aR)-tert-butyl 4-(4-((E)-(benzamido(methylthio)methylene)amino)-5-(ethoxycarbonyl)-1H-pyrrol-3-yl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

(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

1(S)-1-C-[3-(1-benzamido-1-methylthio-methyleneamino)-2-ethoxycarbonyl-4-pyrrolyl]-N-tert-butoxycarbonyl-1,4,5-trideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol

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