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

Base Information

• Chemical Name: 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
• CAS No.: 811419-67-7
• Molecular Formula: C₂₆H₂₈N₂O₇S
• Molecular Weight: 512.584
• Mol file: 811419-67-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 85.0%

lithium methanolate (865-34-9) + 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 (811419-65-5) → 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:

In methanol;

DOI:10.1002/anie.200460218

Reference yield: 85.0%

methanol (67-56-1) + 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 (811419-65-5) → 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:

methanol; With lithium;

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; at 20 ℃; for 16h;

DOI:10.1021/jo040292c

Reference yield:

(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene (160309-18-2) → 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 4 steps

1.1: 68 percent / activated silica gel / 48 h / 70 °C

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

3.1: 1.54 g / I₂; NaHCO₃ / tetrahydrofuran / 16 h / 20 °C

4.1: Li

4.2: 85 percent / 16 h / 20 °C

With lithium hydroxide; iodine; silica gel; lithium; sodium hydrogencarbonate; In tetrahydrofuran; water; 3.1: Danishefsky iodolactonization;

DOI:10.1021/jo040292c

upstream raw materials:

diazomethane

lithium methanolate

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

methanol

Downstream raw materials:

C₃₆H₄₄N₂O₁₁S