5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one

Base Information

• Chemical Name: 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one
• CAS No.: 1026535-33-0
• Molecular Formula: C₅₁H₅₁NO₁₁
• Molecular Weight: 853.966

Synonyms:5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one

Chemical Property of 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one

There total 17 articles about 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one 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:

4-Benzyloxy-3-[4-benzyloxy-5-ethoxy-7-((1E,3E)-penta-1,3-dienyl)-2,3-dihydro-1H-6-aza-cyclopenta[b]naphthalene-3-carbonyl]-1,7-dimethoxy-5,8-bis-methoxymethoxy-naphthalene-2-carbaldehyde → 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one (1026535-33-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 - 25 ℃; for 20h; Yield given;

DOI:10.1021/ja00153a004

Reference yield:

3,6-bis(ethoxycarbonyl)-2-ethoxy-4-methylpyridine (141903-26-6) → 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one (1026535-33-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) LDA, 3.) EtOH

2: 87 percent / DDQ / CH₂Cl₂ / 0.17 h / 25 °C

3: 93 percent / K₂CO₃, Bu₄NI / dimethylformamide / 6 h / 25 °C

4: t-BuOK, EtOH / CH₂Cl₂ / 7 h / -67 - 25 °C

5: 68 percent / Et₃N, DMAP

6: 5 percent / Dibal-H / tetrahydrofuran; toluene / 3 h / -78 °C

7: 2.) I₂ / 1.) THF, hexane, from -78 deg C to 25 deg C, 12 h, 2.) CH₂Cl₂, 25 deg C, 5 d

8: 1.) Dibal-H, 2.) 1.0 M aq. phosphate buffer / 1.) toluene, -30 deg C, 1 h, 2.) toluene, 25 deg C, 20 min

9: tetrahydrofuran / 2 h / -78 - 0 °C

10: imidazole / dimethylformamide / 22 h / 25 °C

11: 35 percent / Ac₂O / heptane / 47 h / 50 °C

12: 52 percent / K₂CO₃, Bu₄NI / acetone / 53 h / 25 °C

13: Bu₄NF / tetrahydrofuran / 10.5 h / 50 °C

14: DMSO, TFAA / CH₂Cl₂ / 1 h / -78 °C

15: DBU / CH₂Cl₂ / 20 h / -78 - 25 °C

With 1H-imidazole; dmap; phosphate buffer; ethanol; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; acetic anhydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00153a004

Reference yield:

3,6-bis(ethoxycarbonyl)-2,2-diethoxy-4-methyl-1-(methylsulfonyl)-1,2,3,4-tetrahydropyridine (1035804-85-3) → 5,8-bis(methoxymethoxy)-9,9'-bis(phenylmethoxy)-6',7'-dihydro-4,6-dimethoxy-1'-ethoxy-3-hydroxy-3'-(1,3-pentadienyl)spiro<2H-benzindene-2,8'-8'H-cyclopentisoquinolin>-1(3H)-one (1026535-33-0)

Guidance literature:

Multi-step reaction with 16 steps

1: 83 percent / DBU / tetrahydrofuran / 40 h / 70 °C

2: 1.) LDA, 3.) EtOH

3: 87 percent / DDQ / CH₂Cl₂ / 0.17 h / 25 °C

4: 93 percent / K₂CO₃, Bu₄NI / dimethylformamide / 6 h / 25 °C

5: t-BuOK, EtOH / CH₂Cl₂ / 7 h / -67 - 25 °C

6: 68 percent / Et₃N, DMAP

7: 5 percent / Dibal-H / tetrahydrofuran; toluene / 3 h / -78 °C

8: 2.) I₂ / 1.) THF, hexane, from -78 deg C to 25 deg C, 12 h, 2.) CH₂Cl₂, 25 deg C, 5 d

9: 1.) Dibal-H, 2.) 1.0 M aq. phosphate buffer / 1.) toluene, -30 deg C, 1 h, 2.) toluene, 25 deg C, 20 min

10: tetrahydrofuran / 2 h / -78 - 0 °C

11: imidazole / dimethylformamide / 22 h / 25 °C

12: 35 percent / Ac₂O / heptane / 47 h / 50 °C

13: 52 percent / K₂CO₃, Bu₄NI / acetone / 53 h / 25 °C

14: Bu₄NF / tetrahydrofuran / 10.5 h / 50 °C

15: DMSO, TFAA / CH₂Cl₂ / 1 h / -78 °C

16: DBU / CH₂Cl₂ / 20 h / -78 - 25 °C

With 1H-imidazole; dmap; phosphate buffer; ethanol; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; acetic anhydride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00153a004

upstream raw materials:

3,6-bis(ethoxycarbonyl)-2-ethoxy-4-methylpyridine

1-ethoxy-3-(ethoxycarbonyl)-7,8-dihydro-9-hydroxy-6H-cyclopentisoquinolin-8-one

1-ethoxy-3-(ethoxycarbonyl)-5,5a,7,8-tetrahydro-9-hydroxy-6H-cyclopentisoquinolin-8-one

6-Ethoxy-4-(3-oxo-cyclopentylmethyl)-pyridine-2,5-dicarboxylic acid diethyl ester

Downstream raw materials:

C₅₁H₄₉NO₁₁

fredericamycin A

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