183434-04-0 Usage
Description
(S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester is a complex chemical compound characterized by a pyranoindolizine core, which is adorned with hydroxy and carboxylic acid functional groups. It also features an ethyl group and a tert-butyl substituent, which may contribute to its potential applications in various fields. The tert-butyl ester form suggests that this compound could serve as a protecting group in organic synthesis, allowing for the manipulation of its reactivity and selectivity. Further research and testing are necessary to fully understand its properties and possible uses, particularly in pharmaceutical or medicinal chemistry.
Uses
Used in Pharmaceutical or Medicinal Chemistry:
(S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester is used as a potential candidate for pharmaceutical or medicinal applications due to its unique molecular structure and functional groups. Its hydroxy and carboxylic acid groups may enable interactions with biopolymers and macromolecules, making it a promising compound for the development of new drugs or therapies.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester is used as a protecting group to control the reactivity and selectivity of the molecule during chemical reactions. The tert-butyl ester group can be selectively introduced and removed, allowing chemists to carry out a variety of synthetic transformations while protecting the carboxylic acid functionality.
Check Digit Verification of cas no
The CAS Registry Mumber 183434-04-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,3,4,3 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 183434-04:
(8*1)+(7*8)+(6*3)+(5*4)+(4*3)+(3*4)+(2*0)+(1*4)=130
130 % 10 = 0
So 183434-04-0 is a valid CAS Registry Number.
183434-04-0Relevant articles and documents
Practical asymmetric synthesis of (S)-4,ethyl-7,8-dihydro-4-hydroxy-1H- pyrano[3,4-f]indolizine-3,6,10(4H)-trione, a key intermediate for the synthesis of Irinotecan and other camptothecin analogs
Henegar,Ashford,Baughman,Sih,Gu
, p. 6588 - 6597 (2007/10/03)
A practical asymmetric synthesis of (S) 4-ethyl-7,8-dihydro-4-hydroxy- 1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (1), a versatile intermediate for the synthesis of camptothecin analogs, was developed. Commercially available citrazinic acid is converted in four steps into the 2-chloro-6- methoxypyridine 5. An ortho-directed metalation followed by reaction with a formamide produces an aldehyde with the required 2,3,4,6-substituted pyridine (6) with high regioselectivity. After refunctionalization of the aldehyde, the chloropyridine is converted into an ester by a facile palladium-mediated carbonylation reaction. Wittig reaction and racemic osmylation produce the diol 16 which is resolved by an efficient lipase resolution to an ee > 99%, and a one-pot recycle of the unwanted diol enantiomer was developed. A series of high-yielding oxidation and deprotection steps convert (S)-16 into the pyridone 25, which is then converted into 1 with an ee > 99.6%.
