(5S)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-one | 1092082-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (5S)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-one
• 英文别名: (5S)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-1,3-dioxolan-4-one
• CAS: 1092082-00-2
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: OELPKYSQHAXWRZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 (5S)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-one 在 盐酸 作用下， 反应 5.5h， 生成 methyl 4-[9-(6-aminopuryl)]-2(S)-hydroxybutyrate
  参考文献：
  名称：

  EP2230239

  摘要：

  公开号：
• 作为产物：
  描述：

  腺嘌呤 、 (S)-5-(2-羟基乙基)-2,2-二甲基-1,3-二噁烷-4-酮 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47.2%的产率得到(5S)-5-[2-(6-aminopurin-9-yl)ethyl]-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-one
  参考文献：
  名称：

  EP2230239

  摘要：

  公开号：

文献信息

• Method for Preparing 4-[9-(6-Aminopurine)]-2-(S)-Hydroxyl-Butyric Acid Methyl Ester
  申请人：Nan Fajun

  公开号：US20110201810A1

  公开（公告）日：2011-08-18

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV. The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.
• US8247549B2
  申请人：——

  公开号：US8247549B2

  公开（公告）日：2012-08-21
• Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers
  作者：Yang-Ming Zhang、Yu Ding、Wei Tang、Wei Luo、Min Gu、Wei Lu、Jie Tang、Jian-Ping Zuo、Fa-Jun Nan

  DOI：10.1016/j.bmc.2008.09.017

  日期：2008.10

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.
• EP2230239
  申请人：——

  公开号：——

  公开（公告）日：——