(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

Base Information

Chemical Name:(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione
CAS No.:40042-02-2
Molecular Formula:C₁₇H₁₅NO₇
Molecular Weight:345.309
Hs Code.:

(3a<i>S</i>)-6-hydroxy-2,2-dimethyl-(3a<i>r</i>,12a<i>c</i>)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-<i>c</i>;4',5'-<i>j</i>]phenanthridine-5,12-dione

Synonyms:(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

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Chemical Property of (3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

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Technology Process of (3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

There total 3 articles about (3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione 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:

: 29477-83-6,220751-83-7
narciclasine

: 40042-02-2
(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

Guidance literature:: Multi-step reaction with 3 steps

1: HC(OEt)3, TsOH

2: MnO₂ / tetrahydrofuran / Ambient temperature

3: silica gel / tetrahydrofuran

With manganese(IV) oxide; silica gel; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In tetrahydrofuran;

Reference yield:

: 29477-83-6,220751-83-7
narciclasine

: 40042-02-2
(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

: C₂₄H₂₀N₂O₁₀

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide / 8 h / 0 - 20 °C / Inert atmosphere

2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Mitsunobu Displacement;
DOI:10.1021/acs.jnatprod.8b00218

Reference yield:

: 40041-97-2
(2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one

: 62-23-7
4-nitro-benzoic acid

: 40042-02-2
(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

: C₂₄H₂₀N₂O₁₀

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Overall yield = 10 mg; Inert atmosphere;
DOI:10.1021/acs.jnatprod.8b00218