methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-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)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate
CAS No.:186355-59-9
Molecular Formula:C₂₇H₃₂N₂O₉S
Molecular Weight:560.625
Hs Code.:

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

There total 11 articles about methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-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: 87.0%

: 124-63-0
methanesulfonyl chloride

: 186355-58-8
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

: 186355-59-9
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: With pyridine; 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

: 186355-59-9
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-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 6 steps

1.1: 88 percent / NaH / dimethylformamide / 1 h / 0 °C

2.1: 12 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

3.1: 82 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 1 h / 0 °C

4.1: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

5.1: HCl / methanol / 1 h / 0 °C

5.2: 57 percent / tetrahydrofuran / 2 h / Heating

6.1: 87 percent / pyridine / 2 h / 0 °C

With pyridine; hydrogenchloride; methanol; lithium methanolate; water; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Dieckmann condensation / 3.1: methanolysis / 4.1: Hydrolysis / 5.1: deprotection / 5.2: alkoxycarbonylation / 6.1: mesylation;
DOI:10.1021/ja962431g

Reference yield:

: (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

: 186355-59-9
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-[(methanesulfonyl)oxy]-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 6 steps

1.1: 14 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2.1: 70 percent / LDA / tetrahydrofuran / 6 h / -78 °C

3.1: 78 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 0.5 h / 0 °C

4.1: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

5.1: HCl / methanol / 1 h / 0 °C

5.2: 57 percent / tetrahydrofuran / 2 h / Heating

6.1: 87 percent / pyridine / 2 h / 0 °C

With pyridine; hydrogenchloride; methanol; lithium methanolate; water; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1.1: Dieckmann condensation / 2.1: Isomerization / 3.1: methanolysis / 4.1: Hydrolysis / 5.1: deprotection / 5.2: alkoxycarbonylation / 6.1: mesylation;
DOI:10.1021/ja962431g