(2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

Base Information

• Chemical Name: (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline
• CAS No.: 174956-25-3
• Molecular Formula: C₄₂H₆₀N₄O₉Si
• Molecular Weight: 793.045

Synonyms:(2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

Chemical Property of (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

Chemical Property:

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Useful:

Technology Process of (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

There total 5 articles about (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline 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: 81.0%

(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[N-(tert-butyloxycarbonyl)-N-[1-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]ethyl]amino]-5-cyano-1,2,3,4-tetrahydroquinoline → (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline (174956-25-3)

Guidance literature:

With lithium diisopropyl amide;

DOI:10.1021/ja953777e

Reference yield: 70.0%

(2R,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline (174956-22-0) → (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline (174956-25-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 8h;

DOI:10.1021/ja962431g

Reference yield: 65.0%

(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[N-(tert-butyloxycarbonyl)-N-[1-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]ethyl]amino]-5-cyano-1,2,3,4-tetrahydroquinoline → (2S,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline (174956-25-3) + (2R,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline (174956-22-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 8h;

DOI:10.1021/ja962431g

upstream raw materials:

(2R,8S)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

(2'RS,4S)-3-(2'-bromopropanoyl)-4-(1-methylethyl)-oxazolidin-2-one

(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

Downstream raw materials:

methyl (2S,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-1-imino-2-methyl-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

duocarmycin A

methyl (2R,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-1-imino-2-methyl-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

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