7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

Base Information

Chemical Name:7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester
CAS No.:167167-34-2
Molecular Formula:C₃₃H₃₅NO₉
Molecular Weight:589.642
Hs Code.:

Synonyms:7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

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Chemical Property of 7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

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Technology Process of 7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

There total 10 articles about 7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-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: 75.0%

: 167167-33-1
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

: 167167-34-2
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 13 ℃;
DOI:10.1248/cpb.43.1064

Reference yield: 4.0%

: 167167-33-1
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

: 167167-34-2
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

: 7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-hydroxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 13 ℃; for 8h;
DOI:10.1248/cpb.46.559

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 167167-34-2
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 2-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 52 percent / TfOH / CH₂Cl₂; cyclohexane / 14 h / 26 °C

2: 7 percent / DIBAL / toluene / 1 h / -76 - -63 °C

3: 75 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h / Heating

4: 78 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -71 - -66 °C

5: 86 percent / Dess-Martin reagent / CH₂Cl₂ / 5 h / Heating

6: 86 percent / tert-BuOK / tetrahydrofuran / 3 h / 23 °C

7: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 44 h / 20 °C

8: 97 percent / pyridine / CH₂Cl₂ / 5 h / 16 °C

9: 75 percent / H₂ / 10percent Pd/C / ethyl acetate / 8 h / 13 °C

With pyridine; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; ethyl acetate; toluene;
DOI:10.1248/cpb.46.559