乙酮,1-[(2R,3R)-3-苯基-2-噁丙环基]-,rel- | 258834-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙酮,1-[(2R,3R)-3-苯基-2-噁丙环基]-,rel-
• 英文名称: 6-O-tert-butyldimethylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-allose propane-1,3-diyl dithioacetal
• 英文别名: [(3aS,4R,6R,6aR)-4-(1,3-dithian-2-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 258834-87-6
• 化学式: C₁₈H₃₅NO₃S₂Si
• 分子量: 405.698
• InChiKey: PLSRDTLEOULSBY-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酮,1-[(2R,3R)-3-苯基-2-噁丙环基]-,rel- 在 mercuric triflate 、 calcium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 52.0h， 生成 (3aR,4R,6R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2
• 作为产物：
  描述：

  1,3-二噻烷 、 5-O-tert-butyldimethylsilyl-1,N-dehydro-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-ribitol 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到乙酮,1-[(2R,3R)-3-苯基-2-噁丙环基]-,rel-
  参考文献：
  名称：

  Transition state analogue inhibitors of protozoan nucleoside hydrolases

  摘要：

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00210-2

文献信息

• Transition state analogue inhibitors of protozoan nucleoside hydrolases
  作者：Richard H. Furneaux、Vern L. Schramm、Peter C. Tyler

  DOI：10.1016/s0968-0896(99)00210-2

  日期：1999.11

  Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C-bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K-i values in the range 0.2-22 mu M against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd. All rights reserved.