(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Base Information

Chemical Name:(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
CAS No.:28245-31-0
Molecular Formula:C₁₅H₁₅NO₇
Molecular Weight:321.287
Hs Code.:

Synonyms:(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

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Chemical Property of (2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

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Technology Process of (2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

There total 1 articles about (2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 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: 79.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

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

: 28245-31-0
(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Guidance literature:: In diethyl ether; ethanol; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/acs.jnatprod.8b00218

Reference yield: 20.0%

: 28245-31-0
(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

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

Guidance literature:: With lithium chloride; In N,N-dimethyl-formamide; at 120 ℃; for 4h;
DOI:10.1021/jo020129m

Reference yield:

: 28245-31-0
(2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

: 29477-83-6,220751-83-7
(2R,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3: L-Selectride / tetrahydrofuran; dichloromethane / 0 - 20 °C / Inert atmosphere

4: water; hydrogenchloride / tetrahydrofuran; dichloromethane / 0 °C / Inert atmosphere

5: chloro-trimethyl-silane; potassium iodide / acetonitrile / 1 h / 60 °C / Inert atmosphere

With hydrogenchloride; chloro-trimethyl-silane; water; L-Selectride; Dess-Martin periodane; toluene-4-sulfonic acid; potassium iodide; In tetrahydrofuran; dichloromethane; acetonitrile; 2: |Dess-Martin Oxidation;
DOI:10.1021/acs.jnatprod.8b00218