(1R,2R,3S,4R)-{4-[(5-amino-6-chloropyrimidin-4-yl)amino]-2,3-[(dimethylmethylene)dioxy]cyclopent-1-yl}methanol | 202267-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1R,2R,3S,4R)-{4-[(5-amino-6-chloropyrimidin-4-yl)amino]-2,3-[(dimethylmethylene)dioxy]cyclopent-1-yl}methanol
• 英文别名: ((3aR,4R,6R,6aS)-6-((5-amino-6-chloropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol；[(3aS,4R,6R,6aR)-4-[(5-amino-6-chloropyrimidin-4-yl)amino]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]methanol
• CAS: 202267-17-2
• 化学式: C₁₃H₁₉ClN₄O₃
• 分子量: 314.772
• InChiKey: QRBDYNIGNORYIW-ZXZZCXTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R)-{4-[(5-amino-6-chloropyrimidin-4-yl)amino]-2,3-[(dimethylmethylene)dioxy]cyclopent-1-yl}methanol 在 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3aS,4R,6R,6aR)-[6-(6-chloropurin-9-yl)-2,2-dimethyltetrahydrocyclopenta[1,3]dioxol-4-yl]methanol
  参考文献：
  名称：

  [EN] PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER
  [FR] DÉRIVÉS DE PURINE EN TANT QU'INHIBITEURS DE CD73 POUR LE TRAITEMENT DU CANCER

  摘要：

  提供的是新颖化合物、其药学上可接受的盐以及其药物组合物，这些化合物是CD73的抑制剂，并可用于癌症治疗。

  公开号：

  WO2015164573A1
• 作为产物：
  描述：

  (1R,2S,3R,4R)-2,3-二羟基-4-(羟甲基)-1-氨基环戊烷水电氯化物 在 对甲苯磺酸 、 三乙胺 作用下， 以 丙酮 、 叔丁醇 为溶剂， 生成 (1R,2R,3S,4R)-{4-[(5-amino-6-chloropyrimidin-4-yl)amino]-2,3-[(dimethylmethylene)dioxy]cyclopent-1-yl}methanol
  参考文献：
  名称：

  [EN] PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER
  [FR] DÉRIVÉS DE PURINE EN TANT QU'INHIBITEURS DE CD73 POUR LE TRAITEMENT DU CANCER

  摘要：

  提供的是新颖化合物、其药学上可接受的盐以及其药物组合物，这些化合物是CD73的抑制剂，并可用于癌症治疗。

  公开号：

  WO2015164573A1

文献信息

• Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin
  作者：Yuko Tokoro、Yuichi Kobayashi

  DOI：10.1039/a901819k

  日期：——

  A 2-furyl group was used as a synthetic equivalent of the CH2OH at the 4′ position of aristeromycin, and dihydroxylation of the cyclopentene possessing the furyl group proceeded highly stereoselectively to produce the key diol for the synthesis of (–)-aristeromycin.

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。
• Purine derivatives as CD73 inhibitors for the treatment of cancer
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：US10654884B2

  公开（公告）日：2020-05-19

  Provided are novel purine nucleoside/nucleotide analogues compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are inhibitors of CD73 and are useful in the treatment of cancer.

  本文提供了新型嘌呤核苷/核苷酸类似物化合物、其药学上可接受的盐及其药物组合物，它们是 CD73 的抑制剂，可用于治疗癌症。
• Highly Stereoselective Synthesis of Aristeromycin through Dihydroxylation of 4-Aryl-1-azido-2-cyclopentenes
  作者：Takauki Ainai、Yong-Gang Wang、Yuko Tokoro、Yuichi Kobayashi

  DOI：10.1021/jo034672u

  日期：2004.2.1

  Dihydroxylation of 4-aryl-1-azido-2-cyclopentenes 6, in which an aryl group is used as a synthetic equivalent of CH2OH, was studied to improve the low to moderate stereoselectivity previously reported for cyclopentenes 3 possessing CH2X and nitrogen atom-containing groups. 2-Furyl, Ph, and p-MeOC6H4 groups were chosen as the aryl groups. Compounds 6a-c possessing such aryl groups were prepared by CuCN-catalyzed reaction between 2-cyclopentene-1,4-diol monoacetate 9 and the corresponding Grignard reagents followed by substitution of the hydroxyl group with (PhO)(2)P(=O)N-3. The desired diols 7a-c were obtained with higher selectivities of > 7:1 when dihydroxylation of 6a-c was carried out at 0degreesC with OsO4 (catalyst) and NMO in a mixed solvent of MeCN, THF, t-BuOH, and H2O. Among them, the furyl compound recorded the highest selectivity of 14:1. The furyl and azido groups on diol 7a were converted into hydroymethyl and adeninyl groups, respectively, to produce acetonide 2, which upon hydrolysis affords aristeromycin 1.
• PURINE DERIVATIVES AS CD73 INHIBITORS FOR THE TREATMENT OF CANCER
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP3134411B1

  公开（公告）日：2021-06-30