3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

Base Information

Chemical Name:3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde
CAS No.:915782-61-5
Molecular Formula:C₂₉H₃₂N₂O₅
Molecular Weight:488.583
Hs Code.:

3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1<i>H</i>,5a<i>H</i>-6,12a-diaza-indeno[7,1-<i>cd</i>]fluorene-6-carbaldehyde

Synonyms:3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

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Chemical Property of 3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

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Technology Process of 3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

There total 16 articles about 3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde 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: 85.0%

: trifluoro-methanesulfonic acid 3a-(2-benzyloxy-ethyl)-6-formyl-7,8-dimethoxy-12-oxo-2,3,3a,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluoren-4-yl ester

: 915782-61-5
3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

Guidance literature:: With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾;
DOI:10.1016/j.tetlet.2006.08.115

Reference yield:

: 915782-46-6
1-benzyloxy-oct-7-yn-4-one

: 915782-61-5
3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1.1: TsOH / benzene / Heating

2.1: 78 percent / nBuLi; MgBr₂ / tetrahydrofuran / -78 - 0 °C

3.1: 75 percent / tBuLi; CuBr*Me₂S / tetrahydrofuran / -78 °C

4.1: 85 percent / MeLi / tetrahydrofuran / -78 °C

5.1: 84 percent / Zn(Cu) / tetrahydrofuran / -45 °C

6.1: 87 percent / nBu₃SnH; Et₃B / benzene / Heating

7.1: 85 percent / p-TsOH / acetone / 20 °C

8.1: 88 percent / benzene / 20 °C

9.1: pyrrolidine; aq. AcOH / propan-2-ol

10.1: iBuOCOCl; Et₃N / tetrahydrofuran / 0 °C

11.1: NaH / dimethylformamide / 0 °C

11.2: KHMDS; TMSCl / tetrahydrofuran / -78 °C

11.3: O₂ / Pd(OAc)2 / dimethylformamide / 60 °C

12.1: 90 percent / 20 °C

13.1: 85 percent / KHMDS / tetrahydrofuran / -78 °C

14.1: 85 percent / Bu₃SnH / Pd(PPh₃)4

With pyrrolidine; n-butyllithium; zinc copper; copper(I) bromide dimethylsulfide complex; triethyl borane; methyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; magnesium bromide; isobutyl chloroformate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene; 5.1: Marino annulation reaction / 11.3: Saegusa reaction / 14.1: Stille reduction;
DOI:10.1016/j.tetlet.2006.08.115

Reference yield:

: 915782-47-7
2-(3-benzyloxy-propyl)-2-but-3-ynyl-[1,3]dioxolane

: 915782-61-5
3a-(2-benzyloxy-ethyl)-7,8-dimethoxy-12-oxo-2,3,3a,11,12,12b-hexahydro-1H,5aH-6,12a-diaza-indeno[7,1-cd]fluorene-6-carbaldehyde

Guidance literature:: Multi-step reaction with 13 steps

1.1: 78 percent / nBuLi; MgBr₂ / tetrahydrofuran / -78 - 0 °C

2.1: 75 percent / tBuLi; CuBr*Me₂S / tetrahydrofuran / -78 °C

3.1: 85 percent / MeLi / tetrahydrofuran / -78 °C

4.1: 84 percent / Zn(Cu) / tetrahydrofuran / -45 °C

5.1: 87 percent / nBu₃SnH; Et₃B / benzene / Heating

6.1: 85 percent / p-TsOH / acetone / 20 °C

7.1: 88 percent / benzene / 20 °C

8.1: pyrrolidine; aq. AcOH / propan-2-ol

9.1: iBuOCOCl; Et₃N / tetrahydrofuran / 0 °C

10.1: NaH / dimethylformamide / 0 °C

10.2: KHMDS; TMSCl / tetrahydrofuran / -78 °C

10.3: O₂ / Pd(OAc)2 / dimethylformamide / 60 °C

11.1: 90 percent / 20 °C

12.1: 85 percent / KHMDS / tetrahydrofuran / -78 °C

13.1: 85 percent / Bu₃SnH / Pd(PPh₃)4

With pyrrolidine; n-butyllithium; zinc copper; copper(I) bromide dimethylsulfide complex; triethyl borane; methyllithium; tert.-butyl lithium; tri-n-butyl-tin hydride; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; magnesium bromide; isobutyl chloroformate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; isopropyl alcohol; acetone; benzene; 4.1: Marino annulation reaction / 10.3: Saegusa reaction / 13.1: Stille reduction;
DOI:10.1016/j.tetlet.2006.08.115