18-hydroxycamptothecin

Base Information

• Chemical Name: 18-hydroxycamptothecin
• CAS No.: 116139-46-9
• Molecular Formula: C₂₀H₁₆N₂O₅
• Molecular Weight: 364.357
• Mol file: 116139-46-9.mol

Synonyms:1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-hydroxy-4-(2-hydroxyethyl)-, (S)- (9CI); 18-Hydroxycamptothecin

Chemical Property of 18-hydroxycamptothecin

Chemical Property:

• Vapor Pressure: 1.05E-28mmHg at 25°C
• Boiling Point: 823.4°Cat760mmHg
• Flash Point: 451.8°C
• PSA: 101.65000
• Density: 1.6g/cm³
• LogP: 1.05200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 18-hydroxycamptothecin

There total 8 articles about 18-hydroxycamptothecin 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:

ethyl 2-(6′-cyan-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate (58610-65-4) → 18-hydroxy-(20RS)-camptothecin (177611-75-5,116139-46-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / t-BuOK / dimethylformamide / 60 h / 50 °C

2: 92 percent / Raney nickel / acetic acid / 3 h / 45 °C

3: 1) NaNO₂ / 1) AcOH, 0 deg C, 4 h, 2) CCl₄, reflux, 12 h

4: 1) LiOH, 2) AcOH / 1) MeOH, H₂O, room temperature, 1 h, 2) CH₂Cl₂, room temperature, 14 h

5: 1) t-BuOK, (EtO)3P, O₂, 2) PPTS / 1) DMF, 0 deg C, 3 h, 2) EtOH, 55 deg C, 7 h

6: TFA / 4 h / Ambient temperature

7: p-TsOH / toluene / 4 h / Heating

With lithium hydroxide; potassium tert-butylate; oxygen; pyridinium p-toluenesulfonate; nickel; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; sodium nitrite; triethyl phosphite; In acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0960-894X(96)00132-1

Reference yield:

C15H17NO7 (177611-73-3) → 18-hydroxy-(20RS)-camptothecin (177611-75-5,116139-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 4 h / Ambient temperature

2: p-TsOH / toluene / 4 h / Heating

With toluene-4-sulfonic acid; trifluoroacetic acid; In toluene;

DOI:10.1016/0960-894X(96)00132-1

Reference yield:

C20H25NO7 (177611-72-2) → 18-hydroxy-(20RS)-camptothecin (177611-75-5,116139-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) t-BuOK, (EtO)3P, O₂, 2) PPTS / 1) DMF, 0 deg C, 3 h, 2) EtOH, 55 deg C, 7 h

2: TFA / 4 h / Ambient temperature

3: p-TsOH / toluene / 4 h / Heating

With potassium tert-butylate; oxygen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; triethyl phosphite; In toluene;

DOI:10.1016/0960-894X(96)00132-1

upstream raw materials:

4-Hydroxy-4-(2-methoxy-ethyl)-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

(E)-N-(2-aminobenzylidene)-4-methylaniline

4-Hydroxy-4-(2-hydroxy-ethyl)-1,4,7,8-tetrahydro-pyrano[3,4-f]indolizine-3,6,10-trione

ethyl 2-(6′-cyan-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)acetate

Refernces

• 1、 Wall, Monroe E.,Wani, Mansukh C.,Nicholas, Allan W.,Manikumar, Govindarajan,Tele, Chhagan,et al.. "Plant Antitumor Agents. 30. Synthesis and Structure Activity of Novel Camptothecin Analogs". . p. 2689 - 2700. Retrieved 2007/10/02.