7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Base Information

Chemical Name:7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester
CAS No.:207739-46-6
Molecular Formula:C₂₈H₃₄N₂O₁₁S
Molecular Weight:606.651
Hs Code.:

Synonyms:7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

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Chemical Property of 7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

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Technology Process of 7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

There total 12 articles about 7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-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: 96.0%

: 124-63-0
methanesulfonyl chloride

: 167167-36-4
7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-hydroxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

: 207739-46-6
7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -18 ℃; for 1h;
DOI:10.1248/cpb.46.559

Reference yield:

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

: 207739-46-6
7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 44 h / 20 °C

7: 97 percent / pyridine / CH₂Cl₂ / 5 h / 16 °C

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

9: 1.) DPPA, i-Pr₂NEt / 1.) benzene, reflux, 18 h, 2.) benzene, reflux, 8 h

10: 69 percent / 3 h / Heating

11: 19 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / 15 h / 20 °C

12: 96 percent / Et₃N / CH₂Cl₂ / 1 h / -18 °C

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

Reference yield:

: 167167-25-1
(S)-3,4-Bis-benzyloxy-butyraldehyde

: 207739-46-6
7-(3-Acetoxy-propoxy)-4-((S)-2-benzyloxy-3-methanesulfonyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 78 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -71 - -66 °C

2: 86 percent / Dess-Martin reagent / CH₂Cl₂ / 5 h / Heating

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

4: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 44 h / 20 °C

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

6: 75 percent / H₂ / 10percent Pd/C / ethyl acetate / 8 h / 13 °C

7: 1.) DPPA, i-Pr₂NEt / 1.) benzene, reflux, 18 h, 2.) benzene, reflux, 8 h

8: 69 percent / 3 h / Heating

9: 19 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / 15 h / 20 °C

10: 96 percent / Et₃N / CH₂Cl₂ / 1 h / -18 °C

With pyridine; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; potassium tert-butylate; hydrogen; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; ethanethiol; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1248/cpb.46.559