3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester
• CAS No.: 811419-63-3
• Molecular Formula: C₂₆H₂₈N₂O₆S
• Molecular Weight: 496.584
• Mol file: 811419-63-3.mol

Synonyms:3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester

Chemical Property of 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester

There total 1 articles about 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl 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: 68.0%

indole-2-carboxylic acid methyl ester (1202-04-6) + (1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (160309-18-2) → 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester (811419-63-3)

Guidance literature:

With silica gel; at 70 ℃; for 48h;

DOI:10.1002/anie.200460218

Reference yield: 95.0%

3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester (811419-63-3) → 3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid (811419-64-4)

Guidance literature:

With lithium hydroxide; In water; at 20 ℃; for 12h;

DOI:10.1002/anie.200460218

Reference yield:

3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid methyl ester (811419-63-3) → 3-[(1aR,2R,3R,3aS,6aS,6bR)-5,5-Dimethyl-3-(toluene-4-sulfonylamino)-hexahydro-1,4,6-trioxa-cyclopropa[e]inden-2-yl]-1H-indole-2-carboxylic acid methyl ester (811419-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide / tetrahydrofuran; H₂O / 14 h / 20 °C

2.1: 1.54 g / I₂; NaHCO₃ / tetrahydrofuran / 16 h / 20 °C

3.1: Li

3.2: 85 percent / 16 h / 20 °C

With lithium hydroxide; iodine; lithium; sodium hydrogencarbonate; In tetrahydrofuran; water; 2.1: Danishefsky iodolactonization;

DOI:10.1021/jo040292c

upstream raw materials:

indole-2-carboxylic acid methyl ester

(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

Downstream raw materials:

3-[(3aS,4R,5R,7aR)-2,2-Dimethyl-4-(toluene-4-sulfonylamino)-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-1H-indole-2-carboxylic acid

N-((3aS,4S,4aR,11cR,12R,12aS)-4-Iodo-2,2-dimethyl-6-oxo-3a,4,4a,6,7,11c,12,12a-octahydro-1,3,5-trioxa-7-aza-indeno[5,6-c]fluoren-12-yl)-4-methyl-benzenesulfonamide

3-[(1aR,2R,3R,3aS,6aS,6bR)-5,5-Dimethyl-3-(toluene-4-sulfonylamino)-hexahydro-1,4,6-trioxa-cyclopropa[e]inden-2-yl]-1H-indole-2-carboxylic acid methyl ester

C₃₆H₄₄N₂O₁₁S