{"title":"合成抗肿瘤药物 (2R,3R,4S,5R)-5-(6-氨基-2-氯嘌呤-9-基)-4-氟-2-(羟甲基)氧杂戊环-3-醇(氯法拉滨)的简单高效途径","authors":"Laxmi Kumari Nagarapu, Chithaluri Sudhakar, Suresh Babu Namani","doi":"10.2174/0115701786287468240209105224","DOIUrl":null,"url":null,"abstract":": Clofarabine (1) is an anticancer agent used to treat acute leukemia. This work discloses the efforts to develop a convenient, environmentally benign, and high-yielding synthetic protocol leading to Clofarabine (1). The synthesis includes bromination of 2-deoxy-2-β-fluoro-1,3,5-tri-O-benzoyl-1- α-D-ribofuranose (6), followed by C-N coupling with a 2,6-dichloro purine (4) and selective amination consecutively. The proposed total synthesis comprises five steps to afford an overall yield of 65- 70% with 99.85% purity. The present process provides preparation of Clofarabine (1) using a simple purification process with lesser reaction time, better yield, and purity without using toxic and pyrophoric chemicals.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7000,"publicationDate":"2024-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A Simple and Efficient Path for the Synthesis Antineoplastic Agent (2R,3R,4S,5R)-5-(6-Amino-2-Chloropurin-9-yl)-4-Fluoro-2-(Hydroxymethyl) oxolan-3-ol (Clofarabine)\",\"authors\":\"Laxmi Kumari Nagarapu, Chithaluri Sudhakar, Suresh Babu Namani\",\"doi\":\"10.2174/0115701786287468240209105224\",\"DOIUrl\":null,\"url\":null,\"abstract\":\": Clofarabine (1) is an anticancer agent used to treat acute leukemia. This work discloses the efforts to develop a convenient, environmentally benign, and high-yielding synthetic protocol leading to Clofarabine (1). The synthesis includes bromination of 2-deoxy-2-β-fluoro-1,3,5-tri-O-benzoyl-1- α-D-ribofuranose (6), followed by C-N coupling with a 2,6-dichloro purine (4) and selective amination consecutively. The proposed total synthesis comprises five steps to afford an overall yield of 65- 70% with 99.85% purity. The present process provides preparation of Clofarabine (1) using a simple purification process with lesser reaction time, better yield, and purity without using toxic and pyrophoric chemicals.\",\"PeriodicalId\":18116,\"journal\":{\"name\":\"Letters in Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.7000,\"publicationDate\":\"2024-02-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Letters in Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.2174/0115701786287468240209105224\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Letters in Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/0115701786287468240209105224","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A Simple and Efficient Path for the Synthesis Antineoplastic Agent (2R,3R,4S,5R)-5-(6-Amino-2-Chloropurin-9-yl)-4-Fluoro-2-(Hydroxymethyl) oxolan-3-ol (Clofarabine)
: Clofarabine (1) is an anticancer agent used to treat acute leukemia. This work discloses the efforts to develop a convenient, environmentally benign, and high-yielding synthetic protocol leading to Clofarabine (1). The synthesis includes bromination of 2-deoxy-2-β-fluoro-1,3,5-tri-O-benzoyl-1- α-D-ribofuranose (6), followed by C-N coupling with a 2,6-dichloro purine (4) and selective amination consecutively. The proposed total synthesis comprises five steps to afford an overall yield of 65- 70% with 99.85% purity. The present process provides preparation of Clofarabine (1) using a simple purification process with lesser reaction time, better yield, and purity without using toxic and pyrophoric chemicals.
期刊介绍:
Aims & Scope
Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts.
The journal is an essential reading for all organic chemists belonging to both academia and industry.