Silatecan

Base Information

• Chemical Name: Silatecan
• CAS No.: 220913-32-6
• Molecular Formula: C₂₆H₃₀N₂O₅Si
• Molecular Weight: 478.62
• NSC Number: 708298
• UNII: 3YEA04NV6H
• DSSTox Substance ID: DTXSID00176592
• Nikkaji Number: J1.244.637C
• Wikidata: Q27074492
• NCI Thesaurus Code: C64618
• Metabolomics Workbench ID: 153379
• ChEMBL ID: CHEMBL412309
• Mol file: 220913-32-6.mol

Synonyms:1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)- dione, 11-((1,1-dimethylethyl)dimethylsilyl)-4-ethyl-4,9- dihydroxy-, (4S)-;7-t-butyldimethylsilyl-10-hydroxycamptothecin;7-tert-butyldimethylsilyl-10-hydroxycamptothecin;AR 67 cpd;AR-67 cpd;DB 67;DB-67

Chemical Property of Silatecan

Chemical Property:

• Boiling Point: 740°Cat760mmHg
• Flash Point: 401.3°C
• PSA: 101.65000
• Density: 1.32g/cm³
• LogP: 3.50070
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 478.19239860
• Heavy Atom Count: 34
• Complexity: 982

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O
• Recent ClinicalTrials: Study of AR-67 in Adult Patients With Recurrence of Glioblastoma Multiforme (GBM) or Gliosarcoma

Technology Process of Silatecan

There total 23 articles about Silatecan 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: 85.0%

(20S)-10-acetoxy-7-tert-butyldimethylsilylcamptothecin (220913-29-1) → DB-67 (220913-32-6)

Guidance literature:

With water; potassium carbonate; for 3h;

DOI:10.1021/jm000144o

Reference yield: 83.2%

(20S)-10-acetoxy-20-O-acetyl-7-tert-butyldimethylsilylcamptothecin → DB-67 (220913-32-6)

Guidance literature:

With hydrogenchloride; In ethanol; for 24h; Heating;

DOI:10.1016/S0968-0896(02)00437-6

Reference yield: 75.0%

7-tert-butyldimethylsilyl-10-phentylmethoxy-camptothecin (472961-11-8) → DB-67 (220913-32-6)

Guidance literature:

With methyl-phenyl-thioether; trifluoroacetic acid; at 55 ℃; for 10h;

DOI:10.1021/ol026408d

upstream raw materials:

(20S)-10-acetoxy-7-tert-butyldimethylsilylcamptothecin

7-tert-butyldimethylsilyl-10-phentylmethoxy-camptothecin

(20S)-7-tert-butyldimethylsilylcamptothecin N-oxide

tert-butyldimethylsilane

Refernces

• 1、 Xiang, Tian-Xiang,Anderson, Bradley D.. "Stable supersaturated aqueous solutions of silatecan 7-t-butyldimethylsilyl-10-hydroxycamptothecin via chemical conversion in the presence of a chemically modified β-cyclodextrin". . p. 1215 - 1222. Retrieved 2002.
• 2、 Curran, Dennis P,Du. "Palladium-promoted cascade reactions of isonitriles and 6-iodo-N-propargylpyridones: synthesis of mappicines, camptothecins, and homocamptothecins.". . p. 3215 - 3218. Retrieved 2007/10/03.