5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

Base Information

Chemical Name:5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester
CAS No.:167167-30-8
Molecular Formula:C₃₅H₃₅NO₈
Molecular Weight:597.665
Hs Code.:

Synonyms:5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

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Chemical Property of 5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

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Technology Process of 5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

There total 9 articles about 5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-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: 86.0%

: 145739-65-7
5-(2-Bromo-acetyl)-1H-pyrrole-2-carboxylic acid methyl ester

: 167167-27-3
(S)-5,6-Bis-benzyloxy-3-oxo-hexanoic acid benzyl ester

: 167167-30-8
5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 - 23 ℃;
DOI:10.1248/cpb.43.1064

Reference yield:

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

: 167167-30-8
5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

With trifluorormethanesulfonic acid; 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

: 167167-30-8
5-((S)-6,7-Bis-benzyloxy-3-benzyloxycarbonyl-4-oxo-heptanoyl)-1H-pyrrole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

With potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1248/cpb.46.559