183434-04-0

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 183434-04-0
• Molecular Formula: C₁₈H₂₁NO₇
• Molecular Weight: 363.36184
• Mol File: 183434-04-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(183434-04-0)
• EPA Substance Registry System: (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(183434-04-0)

Safety Data

• Hazardous Substances Data: 183434-04-0(Hazardous Substances Data)

Usage

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.

Upstream product

• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 

Downstream Products

• 110351-94-5 (4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 97682-44-5 irinotecan 

Relevant 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

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%.