(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

Base Information

Chemical Name:(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester
CAS No.:410071-97-5
Molecular Formula:C₆₁H₆₈F₃N₅O₁₇S₂
Molecular Weight:1264.36
Hs Code.:

(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

Synonyms:(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

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Chemical Property of (9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

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Technology Process of (9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

There total 10 articles about (9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-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:

: 2182-14-1
vindoline

: 1026621-76-0
(Z)-(9S,11R)-4b-Chloro-9-ethyl-7-(2-nitro-benzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(2,2,2-trifluoro-acetoxy)-4b,5,6,7,8,9,10,11,12,14-decahydro-7,14-diaza-cycloundeca[a]indene-13-carboxylic acid methyl ester

: 410071-97-5
(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1021/ja0177049

Reference yield:

: (+)-2-[(3R,5S)-3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-5-(hydroxymethyl)-1-(methoxycarbonyl)heptyl]-3-(2-hydroxyethyl)indole-1-carboxylic acid tert-butyl ester

: 410071-97-5
(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 84.3 percent / Bu₂SnO; Et₃N / CH₂Cl₂ / 15 h / 20 °C

2: 90 percent / NaHCO₃ / dimethylformamide / 3 h / 80 °C

3: 88.3 percent / DEAD; Ph₃P / toluene / 0.67 h / 20 °C

4: 81.5 percent / K₂CO₃ / dimethylformamide / 22 h / 90 °C

5: 84.5 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

6: 87.8 percent / Me₂N(CH₂)3NMe₂ / acetonitrile; toluene / 1 h / 20 °C

7: 90.3 percent / pyridine / CH₂Cl₂ / 0.33 h / 20 °C

8: t-BuOCl / CH₂Cl₂ / 0.17 h / 0 °C

9: TFA / CH₂Cl₂ / 1 h / 0 - 20 °C

With pyridine; tert-butylhypochlorite; N,N,N'N'-tetramethyl-1,3-propanediamine; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Mitsunobu reaction;
DOI:10.1021/ja0177049

Reference yield:

: 5455-59-4
2-Nitrobenzenesulfonamide

: 410071-97-5
(9S,11R,13S)-9-ethyl-7-(2-nitrobenzenesulfonyl)-11-(toluene-4-sulfonyloxymethyl)-9-(trifluoroacetoxy)-13-(15-vindolinyl)-5,6,7,8,9,10,11,12,13,14-decahydro-7,14-diazacycloundeca[a]indene-13-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 88.3 percent / DEAD; Ph₃P / toluene / 0.67 h / 20 °C

2: 81.5 percent / K₂CO₃ / dimethylformamide / 22 h / 90 °C

3: 84.5 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

4: 87.8 percent / Me₂N(CH₂)3NMe₂ / acetonitrile; toluene / 1 h / 20 °C

5: 90.3 percent / pyridine / CH₂Cl₂ / 0.33 h / 20 °C

6: t-BuOCl / CH₂Cl₂ / 0.17 h / 0 °C

7: TFA / CH₂Cl₂ / 1 h / 0 - 20 °C

With pyridine; tert-butylhypochlorite; N,N,N'N'-tetramethyl-1,3-propanediamine; potassium carbonate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction;
DOI:10.1021/ja0177049