N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Base Information

Chemical Name:N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine
CAS No.:144019-84-1
Molecular Formula:C₂₇H₂₅NO₆
Molecular Weight:459.499
Hs Code.:

Synonyms:N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

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Chemical Property of N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

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Technology Process of N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

There total 2 articles about N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-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: 67.0%

: 144019-83-0
N-<(phenyloxy)carbonyl>-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,7,8,9,10-hexahydrophenanthridine

: 144019-84-1
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25 ℃; for 0.166667h;
DOI:10.1021/ja00049a023

Reference yield:

: 144019-82-9,144071-06-7
N-<(phenyloxy)carbonyl>-10-<(tert-butyldimethylsilyl)oxy>-6a,10a-epoxy-6-ethynyl-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

: 144019-84-1
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) BF₃*Et₂O, H₂O, 2.) SiO₂ / 1.) CHCl₃, 25 deg C, 1.5 h, 2.) CHCl₃, 25 deg C, 12 h

2: 67 percent / m-CPBA, aq. NaHCO₃ / CH₂Cl₂ / 0.17 h / 25 °C

With boron trifluoride diethyl etherate; water; silica gel; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/ja00049a023

Reference yield:

: 144019-84-1
N-<(phenyloxy)carbonyl>-6a,10a-epoxy-6-ethynyl-10-oxo-3-(trimethylacetoxy)-5,6,6a,7,8,9,10,10a-octahydrophenanthridine

: 135106-81-9
C₃₁H₂₇NO₅

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Pd(PPh₃)4, Et₂NH, 2.) CuI / 1.) benzene, 25 deg C, 15 min, 2.) benzene, 25 deg C, 1 h

2: 1.) AgNO₃, 2.) KCN / 1.) THF, EtOH, H₂O, 25 deg C, 1 h, 2.) THF, EtOH, H₂O, 25 deg C, 10 min

3: LDA / toluene; cyclohexane / 0.33 h / -78 °C

4: 58 percent / DMAP / CH₂Cl₂ / 22 h / 25 °C

5: 69 percent / AIBN, n-Bu₃SnH / toluene / 1 h / 80 °C

With dmap; potassium cyanide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; silver nitrate; diethylamine; lithium diisopropyl amide; In dichloromethane; cyclohexane; toluene;
DOI:10.1021/ja00049a023