(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

Base Information

Chemical Name:(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester
CAS No.:186355-97-5
Molecular Formula:C₃₇H₅₃N₃O₈Si
Molecular Weight:695.929
Hs Code.:

(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

Synonyms:(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

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Chemical Property of (2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

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Technology Process of (2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

There total 21 articles about (2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-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:

: 67-56-1
methanol

: (2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-((S)-4-isopropyl-2-oxo-oxazolidine-3-carbonyl)-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-3,6-dicarboxylic acid di-tert-butyl ester

: 186355-97-5
(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

Guidance literature:: With lithium methanolate; In tetrahydrofuran; at 0 ℃; for 0.5h; Yield given;
DOI:10.1021/ja953777e

Reference yield:

: 67-56-1
methanol

: 186355-87-3
(2R,8R)-4-(benzyloxy)-3,6-bis(tert-butyloxycarbonyl)-8-[(tert-butyldimethylsilyl)oxy]-1-imino-2-methyl-2-[[(4R)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline

: 186355-97-5
(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

Guidance literature:: With lithium methanolate; In tetrahydrofuran; at 0 ℃; for 0.5h; Yield given;
DOI:10.1021/ja953777e

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 186355-97-5
(2R,8R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-imino-2-methyl-1,7,8,9-tetrahydro-2H-pyrrolo[3,2-f]quinoline-2,3,6-tricarboxylic acid 3,6-di-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: NaH / tetrahydrofuran / 2 h / 0 °C

3: NH₂NH₂, EtOH / 20 h / 140 °C

4: 95 percent / DMAP / tetrahydrofuran / 4 h / Heating

5: 93 percent / TFA / CH₂Cl₂ / 3 h / -30 - 0 °C

6: NaH / dimethylformamide / 1 h / 0 °C

7: LDA / tetrahydrofuran

8: MeOLi / tetrahydrofuran / 0.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; ethanol; lithium methanolate; sodium hydride; trifluoroacetic acid; hydrazine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja953777e