acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester

Base Information

• Chemical Name: acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester
• CAS No.: 28526-38-7
• Molecular Formula: C₂₀H₁₉NO₁₀
• Molecular Weight: 433.372

Synonyms:acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester

Chemical Property of acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester

Chemical Property:

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Technology Process of acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester

There total 1 articles about acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-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: 29.0%

acetic anhydride (108-24-7) + narciclasine (29477-83-6,220751-83-7) → acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester (28526-38-7)

Guidance literature:

In pyridine; at 20 ℃; for 24h;

DOI:10.1021/np068046e

Reference yield: 85.0%

Dibenzyl phosphite (17176-77-1) + acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester (28526-38-7) → acetic acid 3,4-diacetoxy-7-(bis-benzyloxy-phosphoryloxy)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2-yl ester (1111106-77-4)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; acetonitrile; at -30 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm8013585

Reference yield: 41.0%

1-bromo-perbenzoylated α-glucose + acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester (28526-38-7) → (2S,3R,4S,4aR)-7-{[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2,3,4-triyl triacetate + (2S,3R,4S,4aR)-7-{[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2,3,4-triyl triacetate

Guidance literature:

With silver trifluoromethanesulfonate; allyl-trimethyl-silane; In dichloromethane; toluene; at -78 - 20 ℃;

upstream raw materials:

acetic anhydride

narciclasine

Downstream raw materials:

C₁₄H₁₅NO₈

acetic acid 2,3-diacetoxy-7-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-4-yl ester

acetic acid 2,3-diacetoxy-7-O-(2',3',4',6'-tetra-O-benzoyl-α-D-glucopyranosyl)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-4-yl ester

acetic acid 3,4-diacetoxy-7-(bis-benzyloxy-phosphoryloxy)-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-2-yl ester

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