(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

Base Information

Chemical Name:(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester
CAS No.:178449-39-3
Molecular Formula:C₂₆H₂₃NO₇
Molecular Weight:461.471
Hs Code.:

Synonyms:(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

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Chemical Property of (1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

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Technology Process of (1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

There total 14 articles about (1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl 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: 34.0%

: 108-24-7
acetic anhydride

: 178449-36-0
(3R,3aS,12bR,12cR)-3-Hydroxy-7-oxo-4,5,12b,12c-tetrahydro-3H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

: 178449-39-3
(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

Guidance literature:: With sulfuric acid; In acetic acid; at 50 ℃; for 0.25h;
DOI:10.1021/ja9606440

Reference yield:

: (3aR,4R,5R)-4-iodo-2,3,6,7-tetrahydroindole-3a,5-carbolactone

: 178449-39-3
(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 5 h

3: 45 percent / Bu₃SnH, AIBN / benzene / 16 h / Heating

4: benzene / 7 h / Irradiation

5: 2.) NaBH₄ / 1.) EtOH, RT, 15 min, 2.) EtOH, RT, 1 h

6: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 12 h / Ambient temperature

7: 34 percent / H₂SO₄ / acetic acid / 0.25 h / 50 °C

With sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; benzene;
DOI:10.1021/ja9606440

Reference yield:

: 151071-70-4
(2'S,6R)-1-methoxy-6-(2-azidoethyl)-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene

: 178449-39-3
(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / aq. 6M HCl / methanol

2: 82 percent / I₂, H₂O / tetrahydrofuran / 12 h

3: 90 percent / Ph₃P / tetrahydrofuran / 9 h / Heating

4: 98 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 5 h

6: 45 percent / Bu₃SnH, AIBN / benzene / 16 h / Heating

7: benzene / 7 h / Irradiation

8: 2.) NaBH₄ / 1.) EtOH, RT, 15 min, 2.) EtOH, RT, 1 h

9: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 12 h / Ambient temperature

10: 34 percent / H₂SO₄ / acetic acid / 0.25 h / 50 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; water; iodine; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; benzene;
DOI:10.1021/ja9606440