N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Base Information

Chemical Name:N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine
CAS No.:144019-92-1
Molecular Formula:C₃₆H₃₄N₂O₇Si
Molecular Weight:634.761
Hs Code.:

N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

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Chemical Property of N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

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Technology Process of N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

There total 17 articles about N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine 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:

: C₄₂H₄₈N₂O₇Si₂

: 144019-92-1,144071-10-3
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: With boron trifluoride diethyl etherate; water; In chloroform; at 25 ℃; for 0.166667h; Yield given;
DOI:10.1021/ja00049a023

Reference yield:

: 4746-93-4
1,4-dioxaspiro[4.5]decane-6-carboxylic acid

: 144019-92-1,144071-10-3
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 14 steps

1: 96 percent / DCC, DMAP / CH₂Cl₂ / 14 h / Ambient temperature

2: 87 percent / tetrahydrofuran / 96 h / Heating

3: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

4: 1.) 37percent aq. HCl, 2.) DIBAL, LiAlH₄, 3.) silica gel, O₂

5: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

6: 80 percent / 14 h / 25 °C

7: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

8: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

9: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

10: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

11: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

12: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

13: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

14: BF₃*Et₂O, H₂O / CHCl₃ / 0.17 h / 25 °C

With 2,6-dimethylpyridine; hydrogenchloride; propylamine; dmap; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; water; hydrogen; oxygen; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform;
DOI:10.1021/ja00049a023

Reference yield:

: 13747-72-3
ethyl 1,4-dioxa-spiro[4,5]decane-6-carboxylate

: 144019-92-1,144071-10-3
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-10-hydroxy-3-<(2-nitrobenzyl)oxy>-6-<6-(trimethylsilyl)-3(Z)-hexene-1,5-diynyl>-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 15 steps

1: aq. NaOH / methanol / 15 h / Heating

2: 96 percent / DCC, DMAP / CH₂Cl₂ / 14 h / Ambient temperature

3: 87 percent / tetrahydrofuran / 96 h / Heating

4: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 1 h

5: 1.) 37percent aq. HCl, 2.) DIBAL, LiAlH₄, 3.) silica gel, O₂

6: 88 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 25 °C

7: 80 percent / 14 h / 25 °C

8: 98 percent / K₂CO₃ / methanol / 2 h / 25 °C

9: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 25 °C

10: 89 percent / H₂ / 10percent Pd/C / ethanol / 4 h / 760 Torr

11: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 10 min, 2.) THF, 25 deg C, 1 h

12: 98 percent / tetrahydrofuran / 0.25 h / -78 - 0 °C

13: 1.) Pd(PPh₃)4, n-PrNH₂, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 5 h

14: m-CPBA / CH₂Cl₂ / 1 h / 25 °C

15: BF₃*Et₂O, H₂O / CHCl₃ / 0.17 h / 25 °C

With 2,6-dimethylpyridine; hydrogenchloride; propylamine; dmap; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; water; hydrogen; oxygen; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform;
DOI:10.1021/ja00049a023