(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

Base Information

Chemical Name:(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester
CAS No.:171523-59-4
Molecular Formula:C₃₄H₅₄N₂O₆Si
Molecular Weight:614.898
Hs Code.:

(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

Synonyms:(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

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Chemical Property of (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

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Technology Process of (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

There total 10 articles about (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl 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: 90.0%

: 171523-51-6
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-59-4
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 40 ℃; for 24h;
DOI:10.1021/ja00150a010

Reference yield:

: 171523-56-1
(2S,3aR,7aR)-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-59-4
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 34 percent / potassium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C

2: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

3: 85 percent / xylene / 8 h / Heating

4: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

5: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 12 h

6: 100 percent / imidazole, (dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

7: 90 percent / aq. LiOH*H₂O / tetrahydrofuran; methanol / 24 h / 40 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; potassium hexamethyldisilazane; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; dichloromethane; xylene;
DOI:10.1021/ja00150a010

Reference yield:

: 171523-49-2
(2S,3aR,7S,7aS)-6-oxo-7-pent-4-enyl-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 171523-59-4
(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-(4-((triisopropylsilyl)oxy)butyl)-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / NaBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1.5 h / 40 °C

2: 85 percent / xylene / 8 h / Heating

3: 1.) AD-mix β, 2.) NaIO4 / 1.) T-BuOH, H2O, 5 deg C, 36 h, 2.) t-BuOH, H2O, RT, 45 min

4: 93 percent / NaBH₄ / tetrahydrofuran; methanol / 12 h

5: 100 percent / imidazole, (dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

6: 90 percent / aq. LiOH*H₂O / tetrahydrofuran; methanol / 24 h / 40 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; dichloromethane; xylene;
DOI:10.1021/ja00150a010