174092-77-4

Basic information

• Product Name: 4-Ethyl-8-Methoxy-6-triMethylsilanyl-1H-pyrano[3,4-c]pyridine
• Synonyms: 4-Ethyl-8-Methoxy-6-triMethylsilanyl-1H-pyrano[3,4-c]pyridine
• CAS NO: 174092-77-4
• Molecular Formula: C14H21NO2Si
• Molecular Weight: 263.40754
• Mol File: 174092-77-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Ethyl-8-Methoxy-6-triMethylsilanyl-1H-pyrano[3,4-c]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethyl-8-Methoxy-6-triMethylsilanyl-1H-pyrano[3,4-c]pyridine(174092-77-4)
• EPA Substance Registry System: 4-Ethyl-8-Methoxy-6-triMethylsilanyl-1H-pyrano[3,4-c]pyridine(174092-77-4)

Safety Data

• Hazardous Substances Data: 174092-77-4(Hazardous Substances Data)

Upstream product

• 174092-76-3 3-(2-butenyloxymethyl)-4-iodo-2-methoxy-6-trimethylsilylpyridine 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 170453-55-1 2-methoxy-6-(trimethylsilyl)pyridine 
• 174092-75-2 4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde 
• 453518-21-3 2-Methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde 

Downstream Products

• 110351-92-3 (R)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione 
• 19685-09-7 (S)-10-hydroxycamptothecin 
• 19685-10-0 10-methoxycamptothecin 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 7689-03-4 camptothecin 
• 149882-10-0 lurtotecan 
• 174092-79-6 (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one 
• 828934-85-6 (S)-(+)-20-fluorocamptothecin 
• 828934-85-6 (R)-(-)-20-fluorocamptothecin 
• 828934-85-6 (+/-)-20-fluorocamptothecin 
• 202745-00-4 (R)-(-)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one 
• 174092-78-5 (S)-(+)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one 

Relevant articles and documents

PROCESS FOR PRODUCING TRICYCLIC KETONE

In order to efficiently supply CPT, which is a starting compound of irinotecan hydrochloride and a variety of camptothecin derivatives, by a practical total synthesis, the invention provides a means of efficiently preparing a tricyclic ketone that corresp

A general synthetic approach to the (20s)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl isonitriles

A general and efficient synthesis of (20S)-camptothecin (1a) is reported. A key common intermediate containing the pyridone and lactone (DE) rings of camptothecin and most derivatives was constructed from 2-trimethylsilyl-6-methoxypyridine by a series of metalation reactions and a Heck cyclization to provide an achiral bicyclic enol ether. Sharpless asymmetric dihydroxylation followed by lactol oxidation and iododesilylation produced the key intermediate in 94% enantiomeric excess. Alkylation with prop-argyl bromide and a cascade radical reaction with phenyl isonitrile then produced 1a. About 20 other penta-and hexacyclic analogues of camptothecin with differing single or multiple substituents at C7, C9, C10, C11, and/or C12 were made by changing the propargylating agent and the isonitrile. Included among these are several drug candidates and the approved drugs topotecan and irinotecan. The synthesis of the prodrug irinotecan is a direct one that does not pass through the active metabolite. The use of ortho-trimethylsilyl-substituted isonitriles allows the regioselective synthesis of camptothecin analogues in cases where isomeric mixtures are formed from the parent isonitriles. The synthesis of the derivatives relies on the broad scope and functional group tolerance of the key cascade radical reaction.

Kaskaden-Radikalreaktionen von Isocyaniden: eine zweite Generation der Synthese von (20S)-Camtothecin, Topotecan, Irinotecan und G1-147211C

Keywords: Camptothecin; Isocyanide; Kaskadenreaktionen; Radikale