5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide

Base Information

• Chemical Name: 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide
• CAS No.: 1310012-57-7
• Molecular Formula: C₃₆H₃₃N₃O₁₄
• Molecular Weight: 731.67
• Mol file: 1310012-57-7.mol

Synonyms:5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide

Chemical Property of 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide

There total 6 articles about 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide 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: 15.0%

10-[4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate)-3-nitrobenzyloxy]-5,6-dihydro-4H-benzo[de]quinoline-camptothecin (1310012-58-8) → 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide methyl ester (1310012-59-9) + 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide (1310012-57-7)

Guidance literature:

10-[4-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranuronate)-3-nitrobenzyloxy]-5,6-dihydro-4H-benzo[de]quinoline-camptothecin; With sodium methylate; In methanol; at 20 ℃; for 2h;

With water; In methanol;

With hydrogenchloride; In water;

Reference yield:

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) → 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide methyl ester (1310012-59-9) + 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide (1310012-57-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2 h / 20 °C

1.2: 2 h / Cooling with ice

2.1: titanium(IV) bromide / dichloromethane / 24 h / 20 °C

3.1: silver(l) oxide / acetonitrile / 4 h / 20 °C

4.1: silica gel; sodium tetrahydroborate / isopropyl alcohol; chloroform / 1 h / 0 °C

5.1: triethylamine / dichloromethane / 1 h / 0 °C

6.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

7.1: sodium methylate / methanol / 2 h / 20 °C

With sodium tetrahydroborate; sodium methylate; silica gel; titanium(IV) bromide; caesium carbonate; triethylamine; silver(l) oxide; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

Reference yield:

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-94-6) → 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide methyl ester (1310012-59-9) + 5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide (1310012-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 1 h / 0 °C

2: caesium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

3: sodium methylate / methanol / 2 h / 20 °C

With sodium methylate; caesium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

D-glucurono-6,3-lactone

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

5,6-dihydro-4H-benzo[de]quinoline camptothecin-β-D-glucuronide methyl ester