5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-3-(di-2-propenylamino)phenyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6S,6aS)-

Base Information

• Chemical Name: 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-3-(di-2-propenylamino)phenyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6S,6aS)-
• CAS No.: 188744-89-0
• Molecular Formula: C31H50 N2 O5 Si
• Molecular Weight: 558.82
• Mol file: 188744-89-0.mol

Synonyms:5H-1,3-Dioxolo[4,5-c]pyrrole-5-carboxylicacid,4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-6-[3-(di-2-propenylamino)phenyl]tetrahydro-2,2-dimethyl-,1,1-dimethylethyl ester, (3aR,4R,6S,6aS)- (9CI); 5H-1,3-Dioxolo[4,5-c]pyrrole-5-carboxylicacid,4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-6-[3-(di-2-propenylamino)phenyl]tetrahydro-2,2-dimethyl-,1,1-dimethylethyl ester, [3aR-(3aa,4a,6a,6aa)]-

Chemical Property of 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-3-(di-2-propenylamino)phenyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6S,6aS)-

Chemical Property:

• PSA: 60.47000
• LogP: 7.00520

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-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-3-(di-2-propenylamino)phenyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6S,6aS)-

There total 6 articles about 5H-1,3-Dioxolo4,5-cpyrrole-5-carboxylic acid, 4-(1,1-dimethylethyl)dimethylsilyloxymethyl-6-3-(di-2-propenylamino)phenyltetrahydro-2,2-dimethyl-, 1,1-dimethylethyl ester, (3aR,4R,6S,6aS)- 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + Diallyl-{3-[(3aS,4S,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-phenyl}-amine (188744-84-5) → (3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(3-diallylamino-phenyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-89-0)

Guidance literature:

With triethylamine; In dichloromethane; 1.) 0 deg C, 1 h, 2.) room temperature, 3 h;

DOI:10.1016/S0040-4020(96)01172-6

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) → (3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(3-diallylamino-phenyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-89-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NCS / pentane / 0.5 h / Ambient temperature

2: 1.) BuLi, 2,2,6,6-tetramethylpiperidine / 1.) THF, 0 deg C, 2.) THF, -78 deg C

3: 58 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

4: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

With 2,2,6,6-tetramethyl-piperidine; N-chloro-succinimide; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane;

DOI:10.1016/S0040-4020(96)01172-6

Reference yield:

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole (153172-32-8) → (3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(3-diallylamino-phenyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester (188744-89-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi, 2,2,6,6-tetramethylpiperidine / 1.) THF, 0 deg C, 2.) THF, -78 deg C

2: 58 percent / tetrahydrofuran; diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) room temperature, 30 min

3: 99 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 3 h

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(96)01172-6

upstream raw materials:

di-tert-butyl dicarbonate

Diallyl-{3-[(3aS,4S,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-phenyl}-amine

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

(3aR,4R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-chloro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Downstream raw materials:

(3aR,4R,6S,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-6-(3-nitro-phenyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

(3aS,4S,6R,6aR)-4-(3-Amino-phenyl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester