CAS: 110351-94-5; (S)-4-Ethyl-4-Hydroxy-7,8-Dihydro-1H-Pyrano[3,4-F]Indolizine-3,6,10(4H)-Trione

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柠嗪酸置于palladium On Activated Charcoal Palladium Diacetate,2,2,6,6-Tetramethyl-Piperidine-N-Oxyl,Sodium Hypochlorite,Sodium Tetrahydroborate,四氧化锇,正丁基锂,三甲基氯硅烷,4-Acetoxy-2,2,6,6-Tetramethylpiperidine-1-Oxyl,十二/十四烷基二甲基氧化胺,Popcl3,Ps-30 Catalyst,巴拉松,Potassium Tert-Butylate,四丁基氯化铵,氢气,四甲基氯化铵,碳酸氢钠,Potassium Carbonate,Caesium Carbonate,Sodium Iodide,Potassium Bromide体系中,用 四氢呋喃,甲醇,二氯甲烷,水,二甲基亚砜,N,N-二甲基甲酰胺,甲苯,乙腈,三氟乙酸,叔丁醇 用作溶剂,-30.0~142.0 °C,103.42 Kpa 条件下,反应 271.67H,反应生成7-乙基-10-羟基喜树碱中间体
参考文献: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
标题: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
摘要: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%.
Doi:10.1021/jo970173F

专利信息

专利号:US-8722886-B1
优先权日:2012-11-13
标题:Methods for the total chemical synthesis of enantiomerically-pure 7-(2′-trimethylsilyl)ethyl camptothecin
发明人：CHEN XINGHAI; HAUSHEER FREDERICK H; MALAKHOV ANDREY; KOCHAT HARRY
权利人:CHEN XINGHAI; HAUSHEER FREDERICK H; MALAKHOV ANDREY; KOCHAT HARRY; BIONUMERIK PHARMACEUTICALS INC
摘要:The present invention discloses and claims five (5) novel, highly efficient synthetic routes for the total synthesis of enantiomerically-pure (i.e., 99%) 7-(2′-trimethylsilyl)ethyl camptothecin (BNP1350; Karenitecin; Cositecan). These aforementioned synthetic schemes are the first to disclose the total syntheses of 7-(2′-trimethylsilyl)ethyl camptothecin using a highly novel direct, non-linear and convergent synthetic strategy which involves annealing the key C7-(trimethylsilyl)ethyl side chain-bearing A ring key synthons to an enantiomerically-pure tricyclic pyridone; rather than through the conventional methodology which incorporates the C7-(trimethylsilyl)ethyl side chain as the final synthetic step on a totally synthesized camptothecin parent compound. The current novel synthetic approaches reported herein since utilize desirably functionalized A-ring with preinstalled trimethyl silyl ethyl side chain, the aforementioned synthetic methodologies have a wider scope of making wide range of pharmaceutically relevant A-ring substituted BNP1350 analogs by substituting desirably functionalized nitro or protected amino phenyl carboxy A-ring as the starting material.

专利号:US-7608740-B2
优先权日:2005-08-03
标 题 :Method of synthesizing key intermediates for the production of camptothecin derivatives
发明人：RAO RAMAKRISHNA; RAO ALLA VENKATA RAMA
权利人:AVRA LAB PVT LTD
摘要:The present invention discloses a process for efficient production of 2-amino-5-hydroxypropiophenone corresponding to the AB ring part of camptothecin (CPT) skeleton, which is a key intermediate useful for the total synthesis of camptothecin analogs including 7-Ethyl-10-hydroxy camptothecin and novel intermediates thereof.

专利号:US-12187735-B2
优先权日:2018-09-17
标 题:Matter of composition, synthesis, formulation and application of FL118 platform positions 7 and 9-derived analogues for treatment of human disease
发明人：LING XIANG; LI QINGYONG; LI FENGZHI
权利人:CANGET BIOTEKPHARMA LLC
摘要:Described herein, are the chemical synthesis, matter of compositions, formulation, function, methods and uses of the FL118 platform Positions 7 and/or 9-derived analogues for treating cancer or other human diseases. Compounds derived from chemical modifications of the FL118 platform are employed alone or in combination with other anti-cancer agents to preclude, eliminate or reverse cancer phenotypes. This invention intends to realize unique personalized cancer treatment (personalized precision medicine) through application of a series of structural relevant individual FL118 platform-derived analogues, which target multiple cellular human disease-relevant proteins and their signaling pathways.

专利号:US-2025092058-A1
优先权日:2018-09-17
标 题 :Matter of composition, synthesis, formulation and application of fl 118 platform positions 7 and 9-derived analogues for treatment of human disease
发明人：LING XIANG; LI QINGYONG; LI FENGZHI
权利人:CANGET BIOTEKPHARMA LLC
摘要:Described herein, are the chemical synthesis, compounds, methods and uses of the fluoroaryl-substituted derivatives at the FL118 position 7, which target multiple cellular human disease-relevant proteins and their signaling pathways.

专利号:US-7378555-B2
优先权日:2001-02-21
标 题 :Method of synthesizing camptothecin-relating compounds
发明人：OGAWA TAKANORI; NISHIYAMA HIROYUKI; UCHIDA MIYUKI; SAWADA SEIGO
权利人:YAKULT HONSHA KK
摘要:The present invention is to prepare efficiently 2′-amino-5′-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.

专利号:US-2014135499-A1
优先权日:2012-11-13
标 题 :Methods for the total chemical synthesis of enantiomerically-pure 7-(2'-trimethylsilyl) ethyl camptothecin