2-chloro-5-methyl-4-(2-trimethylsilanylethoxy)pyrimidine | 204636-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-5-methyl-4-(2-trimethylsilanylethoxy)pyrimidine
• 英文别名: 2-chloro-5-methyl-4-(2-trimethylsilanyl-ethoxy)-pyrimidine；2-(2-chloro-5-methylpyrimidin-4-yl)oxyethyl-trimethylsilane
• CAS: 204636-94-2
• 化学式: C₁₀H₁₇ClN₂OSi
• 分子量: 244.796
• InChiKey: CAMAHLJMBBJUBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-5-methyl-4-(2-trimethylsilanylethoxy)pyrimidine 在 sodium hydroxide 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2',3'-二脱氧胸苷
  参考文献：
  名称：

  Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine

  摘要：

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00093-8
• 作为产物：
  描述：

  2,4-二氯-5-甲基嘧啶 、 2-(三甲硅基)乙醇 在 sodium hydride 作用下， 以 正戊烷 为溶剂， 以82%的产率得到2-chloro-5-methyl-4-(2-trimethylsilanylethoxy)pyrimidine
  参考文献：
  名称：

  Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine

  摘要：

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00093-8

文献信息

• WO2008/45484
  申请人：——

  公开号：——

  公开（公告）日：——
• Stereoselective synthesis of 2′,3′-dideoxy-nucleosides via intramolecular glycosylation of phenyl 1-seleno-glycosides. Synthesis of 2′,3′-dideoxythymidine
  作者：Jordi Lluís、MaIsabel Matheu、Sergio Castillón

  DOI：10.1016/s0040-4039(98)00093-8

  日期：1998.3

  4-methoxy and 4-(2-trimethylsilylethoxy)pyrimidine bases were attached to the 5-position of the phenyl 2,3-dideoxy-1-seleno-glycero-pentofuranoside moiety. The presence of the silyl protecting group in the base is necessary to lend to neutral beta-anhydro nucleosides by intramolecular glycosylation. The subsequent ring opening affords 3'-deoxythymidine with complete stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Potent and Orally Bioavailable GPR142 Agonists as Novel Insulin Secretagogues for the Treatment of Type 2 Diabetes
  作者：Narihiro Toda、Xiaolin Hao、Yasuyuki Ogawa、Kozo Oda、Ming Yu、Zice Fu、Yi Chen、Yongjae Kim、Mike Lizarzaburu、Sarah Lively、Shauna Lawlis、Michiko Murakoshi、Futoshi Nara、Nobuaki Watanabe、Jeff D. Reagan、Hui Tian、Angela Fu、Alykhan Motani、Qingxiang Liu、Yi-Jyun Lin、Run Zhuang、Yumei Xiong、Peter Fan、Julio Medina、Leping Li、Masanori Izumi、Ryo Okuyama、Satoshi Shibuya

  DOI：10.1021/ml400186z

  日期：2013.8.8

  GPR142 is a G protein-coupled receptor that is predominantly expressed in pancreatic beta-cells. GPR142 agonists stimulate insulin secretion in the presence of high glucose concentration, so that they could be novel insulin secretagogues with reduced or no risk of hypoglycemia. We report here the optimization of HTS hit compound 1 toward a proof of concept compound 33, which showed potent glucose lowering effects during an oral glucose tolerance test in mice and monkeys.