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

Base Information

Chemical Name:methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate
CAS No.:174873-34-8
Molecular Formula:C₃₇H₅₂N₂O₉Si
Molecular Weight:696.913
Hs Code.:

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

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

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

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

There total 24 articles about methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate 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: 83.0%

: 174873-33-7
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

: 174873-34-8
methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ja962431g

Reference yield:

: 174873-30-4
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

: 174873-34-8
methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / NaH / dimethylformamide / 1 h / 0 °C

2: 12 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

3: 82 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 1 h / 0 °C

4: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

With methanol; lithium methanolate; water; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Alkylation / 2: Dieckmann condensation / 3: methanolysis / 4: Hydrolysis;
DOI:10.1021/ja962431g

Reference yield:

: 186355-57-7
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[N-(tert-butyloxycarbonyl)-N-[1-[[(4R)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]ethyl]amino]-5-cyano-1,2,3,4-tetrahydroquinoline

: 174873-34-8
methyl (2R,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 12 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

2: 82 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 1 h / 0 °C

3: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

With methanol; lithium methanolate; water; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; 1: Dieckmann condensation / 2: methanolysis / 3: Hydrolysis;
DOI:10.1021/ja962431g