(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-F]indolizine-3,6,10(4H)-trione

Base Information

• Chemical Name: (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-F]indolizine-3,6,10(4H)-trione
• CAS No.: 110351-94-5
• Molecular Formula: C13H13NO5
• Molecular Weight: 263.25
• Hs Code.: 2934999090
• European Community (EC) Number: 828-521-6
• UNII: YZ4S6C3GB5
• DSSTox Substance ID: DTXSID30436954
• Nikkaji Number: J442.001B
• Wikidata: Q72474429
• Mol file: 110351-94-5.mol

Synonyms:110351-94-5;(S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE;(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione;(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione;(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione;MFCD09833229;YZ4S6C3GB5;SCHEMBL614060;DTXSID30436954;CS-B1681;EX-A4321;AKOS005145923;1H-Pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 4-ethyl-7,8-dihydro-4-hydroxy-, (4S)-;s10949;DS-14808;(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)trione;(S)-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano-[3,4-f]indolizine-3,6,10(4H)-trione;(S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano-[3,4-f]indolizine-3,6,10(4H)-trione;1H-Pyrano[3,4-f]indolizine-3,6,10(4H)-trione,4-ethyl-7,8-dihydro-4-hydroxy-,(4S)-;4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione, (S)-;(4S)-4-ETHYL-4-HYDROXY-1H,3H,4H,6H,7H,8H,10H-PYRANO[3,4-F]INDOLIZINE-3,6,10-TRIONE;(4S)-4alpha-Ethyl-7,8-dihydro-4beta-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

Chemical Property of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-F]indolizine-3,6,10(4H)-trione

Chemical Property:

• Melting Point: 183-185℃ (decomposition)
• Boiling Point: 666.634 °C at 760 mmHg
• PKA: 11.20±0.20(Predicted)
• Flash Point: 356.968 °C
• PSA: 85.60000
• Density: 1.506 g/cm³
• LogP: 0.08910
• Storage Temp.: 2-8°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 263.07937252
• Heavy Atom Count: 19
• Complexity: 574

Purity/Quality:

99%min. ^*data from raw suppliers

(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CCC(=O)C3=C2)O
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CCC(=O)C3=C2)O
• Uses: (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a key intermediate in the synthesis of Irinotecan (I767500) and Camptothecin (C175150) analogs.

Technology Process of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-F]indolizine-3,6,10(4H)-trione

There total 53 articles about (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-F]indolizine-3,6,10(4H)-trione 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: 100.0%

(S)-4′-ethyl-4′-hydroxy-7′,8′-dihydrospiro[[1,3]dioxolane-2,6′-pyrano[3,4-f]indolizine]-3′,10′(1′H,4′H)-dione (110351-93-4) → (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 60 ℃; for 3h;

DOI:10.1016/0957-4166(95)00154-H

Reference yield: 100.0%

C17H21NO7 (165674-36-2) → (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 60 ℃; for 3h;

DOI:10.1016/0957-4166(95)00154-H

Reference yield: 96.0%

(S,E)-6-benzylidene-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,10(4H,6H)-dione → (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (110351-94-5)

Guidance literature:

(S,E)-6-benzylidene-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,10(4H,6H)-dione; With oxygen; ozone; In dichloromethane; at -40 ℃; for 0.75h;

With dimethylsulfide; In dichloromethane; at -40 - 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2017.04.013

upstream raw materials:

(S)-4′-ethyl-4′-hydroxy-7′,8′-dihydrospiro[[1,3]dioxolane-2,6′-pyrano[3,4-f]indolizine]-3′,10′(1′H,4′H)-dione

(S)-α-ethyl-α-hydroxy-1,1-(ethylenedioxy)-6-hydroxymethyl-5-oxo-1,2,3,5-tetrahydroindolizine-7-acetamide

C₁₇H₂₁NO₇

1,1-dimethylethyl (S)-4-ethyl-3,4,8,10-tetrahydro-4,6-dihydroxy-3,10-dioxo-1H-pyrano[3,4 - f] indolidin-7-carboxylate

Downstream raw materials:

irinotecan

Refernces

• 1、 Jew,Ok,Kim,Kim,Kim,Hah,Cho. "Enantioselective synthesis of 20(S)-camptothecin using Sharpless catalytic asymmetric dihydroxylation". . p. 1245 - 1248. Retrieved 1995.
• 2、 Lackey, Karen,Besterman, Jeffrey M.,Fletcher, Wade,Leitner, Peter,Morton, Bradley,Sternbach, Daniel D.. "Rigid Analogs of Camptothecin as DNA Topoisomerase I Inhibitors". . p. 906 - 911. Retrieved 1995.
• 3、 Wang, Xinlong,Xu, Lingjun,Xiong, Fangjun,Wu, Yan,Chen, Fener. "An improved synthesis of (20S)-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst". . p. 843 - 848. Retrieved 2017/06/13.
• 4、 -. "COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF". Paragraph 0145; 0146. . Retrieved 2015/06/24.