SN38 glucuronide

Base Information

• Chemical Name: SN38 glucuronide
• CAS No.: 121080-63-5
• Molecular Formula: C₂₈H₂₈N₂O₁₁
• Molecular Weight: 568.537
• UNII: D3XLA2EX2N
• DSSTox Substance ID: DTXSID401043702
• Nikkaji Number: J459.944F
• Wikidata: Q27108206
• Metabolomics Workbench ID: 69664
• ChEMBL ID: CHEMBL3526803
• Mol file: 121080-63-5.mol

Synonyms:7-ethyl-10-hydroxycamptothecin glucuronide;SN-38 glucuronide

Chemical Property of SN38 glucuronide

Chemical Property:

• Melting Point: >250°C (dec.)
• PSA: 197.87000
• LogP: -0.08700
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 568.16930971
• Heavy Atom Count: 41
• Complexity: 1190

Purity/Quality:

98%Min ^*data from raw suppliers

SN-38 glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC6C(C(C(C(O6)C(=O)O)O)O)O
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
• Uses: A metabolite of Irinotecan

Technology Process of SN38 glucuronide

There total 4 articles about SN38 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: 59.2%

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (121098-77-9) → SN-38 glucuronide (121080-63-5)

Guidance literature:

With sodium hydroxide; In acetone; for 2h; Ambient temperature;

DOI:10.1248/cpb.40.131

Reference yield:

7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) → SN-38 glucuronide (121080-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.4 percent / K₂CO₃ / acetone / 6 h / Heating

2: 59.2 percent / 0.2 N aq. NaOH / acetone / 2 h / Ambient temperature

With sodium hydroxide; potassium carbonate; In acetone;

DOI:10.1248/cpb.40.131

Reference yield:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → SN-38 glucuronide (121080-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.4 percent / K₂CO₃ / acetone / 6 h / Heating

2: 59.2 percent / 0.2 N aq. NaOH / acetone / 2 h / Ambient temperature

With sodium hydroxide; potassium carbonate; In acetone;

DOI:10.1248/cpb.40.131

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

7-ethyl-10-hydroxycamptothecin

uridine diphosphoglucuronic acid

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Refernces

• 1、 Yaegashi,Nokata,Sawada,Furuta,Yokokura,Miyasaka. "Chemical modification of an antitumor alkaloid, 20(S)-camptothecin: Glycosides, phosphates and sulfates of 7-ethyl-10-hydroxycamptothecin". . p. 131 - 135. Retrieved 2007/10/02.