ChemicalBook > CAS DataBase List >  (S)-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

Product 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
Chemical Name
(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione
Synonyms
(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione;(S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione;RUBI-006;(S)-trione;10(4H)-TRIONE;4-F]INDOLIZINE-3;Trihydroxy lactone;Exatecan Impurity 3;8-DIHYDRO-1H-PYRANO[3;Exatecan intermediates
CBNumber
CB41009288
Molecular Formula
C13H13NO5
Formula Weight
263.25
MOL File
110351-94-5.mol
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(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Property

Melting point:
183-185℃ (decomposition)
Boiling point:
666.6±55.0 °C(Predicted)
Density 
1.50±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
pka
11.20±0.20(Predicted)
InChI
InChI=1S/C13H13NO5/c1-2-13(18)8-5-9-10(15)3-4-14(9)11(16)7(8)6-19-12(13)17/h5,18H,2-4,6H2,1H3/t13-/m0/s1
InChIKey
IGKWOGMVAOYVSJ-ZDUSSCGKSA-N
SMILES
C1(=O)C2N(C(=O)C3COC(=O)[C@@](CC)(O)C=3C=2)CC1
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Safety

HazardClass 
IRRITANT
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC
Product number
E917350
Product name
(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
Packaging
25mg
Price
$10240
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
APN0001932
Product name
(4S)-4-ETHYL-7,8-DIHYDRO-4-HYDROXY-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE
Purity
95.00%
Packaging
5MG
Price
$500.51
Updated
2021/12/16
AK Scientific
Product number
1946AA
Product name
(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
Packaging
25mg
Price
$549
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CCH0004695
Product name
(S)-4-HYDROXY-4-PROPYL-7,8-DIHYDRO-1H-PYRANO-[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE
Purity
95.00%
Packaging
1G
Price
$4480.35
Updated
2021/12/16
Abosyn
Product number
61-5678
Product name
(S)-4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
Purity
95+%
Packaging
0.1g
Price
$4750
Updated
2021/12/16
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(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Chemical Properties,Usage,Production

Chemical Properties

Light yellow solid.

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.

Preparation

Synthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione: Compound (Formula 4) 4.3 g (100 mmol), 200 ml of dichloromethane, 200 ml of 2M sulfuric acid, stirred at room temperature for 2 h, separated the organic layer, washed with saturated brine, dried, recovered dichloromethane to dryness, and recrystallized from isopropanol to obtain S-tricyclic lactone (Formula 1) 1.5 g, mp 172-174°C, [α]D15+115.6° (C=0.5, chloroform), yield 57%.

Application

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione is the key intermediate for the synthesis of a series of (20S)-camptothecin analogues. Since its isolation from the Chinese plant Camptothecaacuminata by Wall et al. In 1966, (20S)-camptothecin, a pent acyclic natural alkaloid, has re-emerged as one of the most important lead compounds for the discovery of new and selective anticancer drugs because of the disclosure of its unique mechanism of action as a selective inhibitor DNA topoisomerase Ⅰ, a process causing irreversible DNA damage and subsequent cell death. Three camptothecin derivatives with high antitumor activity, topotecan, belotecan, and irinotecan, have been launched as anticancer drugs in clinical practice, and many other analogues are at various stages of clinical development.

Clinical claims and research

Camptothecin is a pentacyclic alkaloid extracted from Camptotheca by Wall et al. in the early 1960s. As an anticancer chemical, the compound has quickly attracted people's attention due to its strong inhibitory activity against leukemia and various other malignant tumors in animal experiments. In the total synthesis of camptothecin, The total synthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione is research focus.

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD
Product
(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 110351-94-5
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
25kg
Release date
2022-02-17
Henan Aochuang Chemical Co.,Ltd.
Product
(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione 110351-94-5
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1Ton
Release date
2022-09-30
Qiuxian Baitai New Material Co., LTD
Product
(S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE 110351-94-5
Price
US $403.00/g
Min. Order
1g
Purity
99%
Supply Ability
500ton/Month
Release date
2021-10-15

110351-94-5, (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trioneRelated Search:

L-Pyroglutaminol Trifluoroacetic acid Acetylene Benzene Tenofovir Boric acid D-Ribose 13,14-Didehydromatridin-15-one N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide Exatecan mesilate Irinotecan Lactone IMpurity 11-Desethyl Irinotecan (R)-SN-38 12-ethyl-8-methyl-9-oxo-7-propionyl-9,11-dihydroindolizino[1,2-b]quinolin-2-yl [1,4'-bipiperidine]-1'-carboxylate 7-Ethylcamptothecin 12-Hydroxy Irinotecan 7,11-Diethyl-10-hydroxycaMptothecin sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate

  • (S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-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-, (S)-
  • RUBI-006
  • (4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione
  • (s)-8-Ethyl-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-aza-cyclopenta[b]naphthalene-1,4,7-trione
  • (S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione
  • (S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3
  • (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)-
  • (S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE 110351-94-5
  • (S)-trione
  • (S)-4-ETHYL-4-HYDROXY-7
  • 10(4H)-TRIONE
  • 4-F]INDOLIZINE-3
  • 8-DIHYDRO-1H-PYRANO[3
  • Exatecan intermediates
  • Trihydroxy lactone
  • Exatecan Intermediate 1
  • (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolidin-3,6,10(4H)-trione
  • Exatecan Impurity 3
  • (S) 4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano O [3,4-F] indoleazine-3,6,10 (4) - one
  • Irinotecan Impurity 64
  • 110351-94-5
  • Anti-cancer
  • ADCs Linkers
  • 1