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

Base Information

Chemical Name:7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester
CAS No.:167167-35-3
Molecular Formula:C₃₄H₃₈N₂O₉
Molecular Weight:618.684
Hs Code.:

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

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

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

There total 10 articles about 7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-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: 69.0%

: 67-56-1
methanol

: 1027968-50-8
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-5-isocyanato-1H-indole-2-carboxylic acid methyl ester

: 167167-35-3
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: for 3h; Heating;
DOI:10.1248/cpb.46.559

Reference yield:

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

: 167167-35-3
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 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

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

11: 69 percent / 3 h / Heating

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

Reference yield:

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

: 167167-35-3
7-(3-Acetoxy-propoxy)-4-((S)-2,3-bis-benzyloxy-propyl)-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 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

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