(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpent-4-yne-1,2-diol | 609842-70-8

• 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: (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpent-4-yne-1,2-diol
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-4-yne-1,2-diol
• CAS: 609842-70-8
• 化学式: C₁₂H₂₄O₃Si
• 分子量: 244.406
• InChiKey: HPSCUBOKIMTHMI-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpent-4-yne-1,2-diol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(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
• 作为产物：
  描述：

  (R,E)-3-(2-methyl-1,4-dioxaspiro[4.4]nonan-2-yl)prop-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 N-氯代丁二酰亚胺 、 正丁基锂 、 溶剂黄146 、 (+)-Weinsaeure-diethylester 、 三苯基膦 、 methyloxirane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpent-4-yne-1,2-diol
  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.