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

Base Information

Chemical Name:7-(2-Acetoxy-ethoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester
CAS No.:207739-43-3
Molecular Formula:C₃₉H₃₉NO₉
Molecular Weight:665.74
Hs Code.:

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

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

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

There total 8 articles about 7-(2-Acetoxy-ethoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 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: 97.0%

: 108-24-7
acetic anhydride

: 207739-41-1
4-((S)-2,3-Bis-benzyloxy-propyl)-7-(2-hydroxy-ethoxy)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

: 207739-43-3
7-(2-Acetoxy-ethoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

Guidance literature:: With pyridine; In dichloromethane; at 23 ℃; for 5h;
DOI:10.1248/cpb.46.559

Reference yield:

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

: 207739-43-3
7-(2-Acetoxy-ethoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 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: 41 percent / TMSOTf, 1,2-bis(trimethylsilyloxy)ethane / CH₂Cl₂ / 48 h / 26 °C

8: 97 percent / pyridine / CH₂Cl₂ / 5 h / 23 °C

With pyridine; 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; toluene;
DOI:10.1248/cpb.46.559

Reference yield:

: 167167-24-0
(S)-3,4-Bis-benzyloxy-butyric acid ethyl ester

: 207739-43-3
7-(2-Acetoxy-ethoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-1H-indole-2,5-dicarboxylic acid 5-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2: 75 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h / Heating

3: 78 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -71 - -66 °C

4: 86 percent / Dess-Martin reagent / CH₂Cl₂ / 5 h / Heating

5: 86 percent / tert-BuOK / tetrahydrofuran / 3 h / 23 °C

6: 41 percent / TMSOTf, 1,2-bis(trimethylsilyloxy)ethane / CH₂Cl₂ / 48 h / 26 °C

7: 97 percent / pyridine / CH₂Cl₂ / 5 h / 23 °C

With pyridine; 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1248/cpb.46.559