(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2-methylpent-4-ynal | 609842-63-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2-methylpent-4-ynal
• CAS: 609842-63-9
• 化学式: C₁₂H₂₂O₃Si
• 分子量: 242.39
• InChiKey: YUIAGSMTBCJUOF-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(tert-butyldimethylsiloxy)-2-(dimethoxyphosphoryl)acetate 、 (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2-methylpent-4-ynal 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(S)-3-(tert-butyldimethylsilyloxy)-5-[(R)-1-(tert-butyldimethylsilyloxy)prop-2-ynyl]-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1
• 作为产物：
  描述：

  [(2S,3R)-3-((S)-2-Methyl-1,4-dioxa-spiro[4.4]non-2-yl)-oxiranyl]-methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl N-氯代丁二酰亚胺 、 正丁基锂 、 三氯异氰尿酸 、 溶剂黄146 、 三苯基膦 、 methyloxirane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2-methylpent-4-ynal
  参考文献：
  名称：

  Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase

  摘要：

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01583-1

文献信息

• The total synthesis and biological evaluation of nafuredin-γ and its analogues
  作者：Tohru Nagamitsu、Daisuke Takano、Miyuki Seki、Shiho Arima、Masaki Ohtawa、Kazuro Shiomi、Yoshihiro Harigaya、Satoshi Ōmura

  DOI：10.1016/j.tet.2008.06.066

  日期：2008.8

  Nafuredin (1) is converted to nafuredin-gamma (2) under mild basic conditions and both compounds exhibit the same inhibitory activity and selectivity against NADH-fumarate reductase (complex 1). The total synthesis of 2 was achieved by a convergent approach using Stille coupling. The structural elements required for inhibitory activity against NADH-fumarate reductase (complex I) were then investigated by evaluation of nafuredin-gamma (2) and its structural analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• Total synthesis of nafuredin-γ, a γ-lactone related to nafuredin with selective inhibitory activity against NADH-fumarate reductase
  作者：Tohru Nagamitsu、Daisuke Takano、Kazuro Shiomi、Hideaki Ui、Yuichi Yamaguchi、Rokuro Masuma、Yoshihiro Harigaya、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1016/s0040-4039(03)01583-1

  日期：2003.8

  Nafuredin-gamma (2) converted from nafuredin (1) under mild basic conditions showed the same inhibitory activity and selectivity against NADH-fumarate reductase as 1. Total synthesis of 2, a proposed active form of 1, has been accomplished by a convergent approach using Stille coupling. (C) 2003 Elsevier Ltd. All rights reserved.