Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

Base Information

Chemical Name:Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester
CAS No.:169305-05-9
Molecular Formula:C₂₂H₂₁NO₉
Molecular Weight:443.41
Hs Code.:

Synonyms:Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

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Chemical Property of Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

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Technology Process of Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

There total 14 articles about Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl 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:

: Benzoic acid (3aS,3bR,10bR,11R,12S,12aS)-6-methoxy-2,2-dimethyl-5-oxo-12-sulfooxy-3a,3b,4,5,10b,11,12,12a-octahydro-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-11-yl ester

: 169305-05-9
Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

Guidance literature:: With sulfuric acid; In tetrahydrofuran; Yield given;
DOI:10.1021/ja00145a038

Reference yield:

: (7-methoxybenzo[d][1,3]dioxol-5-yl)magnesium bromide

: 169305-05-9
Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: CuCN / tetrahydrofuran; diethyl ether / 0 °C

2: OsO₄, 4-ethylmorpholine N-oxide*H₂O (NMO*H₂O) / CH₂Cl₂ / Ambient temperature

3: 100 percent / 2,6-lutidine / CH₂Cl₂

4: 75 percent / N-bromosuccinimide / dimethylformamide

5: (CH₃)3P, H₂O / tetrahydrofuran

6: Et₃N / tetrahydrofuran

7: t-BuLi / diethyl ether / -78 °C

8: tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / -78 - 0 °C

9: 1.) SOCl₂, Et₃N, 2.) RuCl₃*H₂O, NaIO₄ / 2.) CCl₄, CH₃CN, H₂O, RT

10: dimethylformamide

11: aq. H₂SO₄ / tetrahydrofuran

With 2,6-dimethylpyridine; ruthenium trichloride; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; thionyl chloride; N-ethylmorpholine N-oxide; sulfuric acid; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; triethylamine; trimethylphosphane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00145a038

Reference yield:

: 169304-97-6
(1S,4R,5S,6R)-4-azido-5,6-(isopropylidenedioxy)cyclohex-2-enyl methyl carbonate

: 169305-05-9
Benzoic acid (1R,2R,3S,4S,4aR,11bR)-2,3,4-trihydroxy-7-methoxy-6-oxo-1,2,3,4,4a,5,6,11b-octahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: CuCN / tetrahydrofuran; diethyl ether / 0 °C

2: OsO₄, 4-ethylmorpholine N-oxide*H₂O (NMO*H₂O) / CH₂Cl₂ / Ambient temperature

3: 100 percent / 2,6-lutidine / CH₂Cl₂

4: 75 percent / N-bromosuccinimide / dimethylformamide

5: (CH₃)3P, H₂O / tetrahydrofuran

6: Et₃N / tetrahydrofuran

7: t-BuLi / diethyl ether / -78 °C

8: tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / -78 - 0 °C

9: 1.) SOCl₂, Et₃N, 2.) RuCl₃*H₂O, NaIO₄ / 2.) CCl₄, CH₃CN, H₂O, RT

10: dimethylformamide

11: aq. H₂SO₄ / tetrahydrofuran

With 2,6-dimethylpyridine; ruthenium trichloride; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; thionyl chloride; N-ethylmorpholine N-oxide; sulfuric acid; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; triethylamine; trimethylphosphane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00145a038