(3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol | 154912-70-6

• 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: (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol
• 英文别名: (R)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-1-ol；(3R)-4-(tert-butyldiphenylsilyloxy)-3-methyl-1-butanol；(R)-4-(tert-Butyldiphenylsilyloxy)-3-methyl-1-butanol；(3R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylbutan-1-ol
• CAS: 154912-70-6
• 化学式: C₂₁H₃₀O₂Si
• 分子量: 342.554
• InChiKey: RKCMDKZBHHXRIQ-GOSISDBHSA-N

物化性质

• 沸点：
  409.7±37.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 在 Lindlar's catalyst 喹啉 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium amide 、 3 A molecular sieve 、 TEA 、 四丁基氟化铵 、 氢气 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 、 碳酸氢钠 、 D-(-)-酒石酸二异丙酯 、 红铝 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 氨 为溶剂， 反应 18.0h， 生成 (2R,5S,7S)-8-Benzyloxy-2-methyl-octane-1,5,7-triol
  参考文献：
  名称：

  针对雷帕霉素合成的研究：C-1至C-15片段的立体选择性合成。

  摘要：

  描述了雷帕霉素的适当官能化的C-1至C-15区段的立体选择性合成。

  DOI：

  10.1016/s0040-4039(00)61612-x
• 作为产物：
  描述：

  (R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 在 sodium hydroxide 、 正丁基锂 、 草酰氯 、 tetrafluoroboric acid-diethyl ether complex 、 双氧水 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol
  参考文献：
  名称：

  Callystatin A（一种来自海洋海绵，Callyspongia truncata的有效的细胞毒性聚酮化合物）的绝对立体结构

  摘要：

  在C中的未识别的配置5和C 10在callystatin A（1），从海洋海绵一个有效的细胞毒性的聚酮化合物Callyspongia截形，被确定为[R ，- [R通过的圆二色性光谱比较1与两个模型化合物2和3。化合物2和3是通过在C 6 = C 7位置进行E选择性Wittig烯化反应作为关键反应合成的。

  DOI：

  10.1016/s0040-4039(97)01194-5

文献信息

• CYCLOPROPANECARBOXYLIC ACID DERIVATIVE
  申请人：Nagata Tsutomu

  公开号：US20130012532A1

  公开（公告）日：2013-01-10

  A compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, wherein R 1 represents a C1 to C6 alkyl group which may be substituted by one to three groups selected from substituent group A, or the like (substituent group A: a hydroxy group, a halogeno group, a cyano group, a nitro group, an amino group, a carboxy group, a C1 to C3 alkyl group, etc.); R 2 , R 3 , and R 8 each independently represent a hydrogen atom or a C1 to C3 alkyl group; R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 each independently represent a hydrogen atom or the like; and R 11 represents a hydrogen atom or the like, has TAFIa enzyme inhibitory activity and is useful as a therapeutic drug for myocardial infarction, angina pectoris, acute coronary syndrome, cerebral infarction, deep vein thrombosis, pulmonary embolism, or the like.

  以下是由下列通式（I）表示的化合物或其药学上可接受的盐，其中R1代表C1至C6烷基，该烷基可以被选自取代基A的一个至三个基团取代（取代基A：羟基、卤素基、氰基、硝基、氨基、羧基、C1至C3烷基等）；R2、R3和R8各自独立地代表氢原子或C1至C3烷基；R4、R5、R6、R7、R9和R10各自独立地代表氢原子或类似物；而R11代表氢原子或类似物。该化合物具有TAFIa酶抑制活性，可用作治疗心肌梗塞、心绞痛、急性冠状动脉综合征、脑梗死、深静脉血栓、肺栓塞等疾病的治疗药物。
• Cobalt versus Osmium: Control of Both <i>trans</i> and <i>cis</i> Selectivity in Construction of the EFG Rings of Pectenotoxin 4
  作者：Ahria Roushanbakhti、Yifan Liu、Paul C. M. Winship、Michael J. Tucker、Wasim M. Akhtar、Daryl S. Walter、Gail Wrigley、Timothy J. Donohoe

  DOI：10.1002/anie.201708278

  日期：2017.11.20

  Two types of oxidative cyclisation reaction, utilising either osmium or cobalt catalysis, provide complete control of the relative stereochemistry of THF rings embedded in the complex pectenotoxin-4 ring system. In this manner, rapid access to either trans (Co) or cis (Os) 2,5-disubstituted THF rings of the natural product molecule was facilitated.

  利用或钴催化的两种类型的氧化环化反应可完全控制嵌入在复杂的果胶毒素4环系统中的THF环的相对立体化学。以这种方式，促进了快速接近天然产物分子的反式（Co）或顺式（Os）2，5-二取代的THF环。
• Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide
  作者：Nobutoshi Murakami、Masanori Sugimoto、Tatsuo Nakajima、Motoyuki Kawanishi、Yasuhiro Tsutsui、Motomasa Kobayashi

  DOI：10.1016/s0968-0896(00)00199-1

  日期：2000.11

  5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally affected the activity, while lack of the 10-methyl group in callystatin A decreased cytotoxicity. In addition, the C-5 epimer and the 8-deethyl analogue of callystatin A showed weaker cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Highly Stereocontrolled Total Synthesis of β-<scp>d</scp>-Mannosyl Phosphomycoketide: A Natural Product from <i>Mycobacterium tuberculosis</i>
  作者：Nan-Sheng Li、Louise Scharf、Erin J. Adams、Joseph A. Piccirilli

  DOI：10.1021/jo4006602

  日期：2013.6.21

  beta-D-Mannosyl phosphomycoketide (C-32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C-32-MPM contains, a C-32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C-32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.
• Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata
  作者：Nobutoshi Murakami、Weiqi Wang、Masashi Aoki、Yasuhiro Tsutsui、Kouichi Higuchi、Shunji Aoki、Motomasa Kobayashi

  DOI：10.1016/s0040-4039(97)01194-5

  日期：1997.8

  The unidentified configurations at C5 and C10 in callystatin A (1), a potent cytotoxic polyketide from the marine sponge Callyspongia truncata, were determined to be R,R by comparing the circular dichroism spectrum of 1 with those of two model compounds 2 and 3. Compounds 2 and 3 were synthesized by using E-selective Wittig olefination at the C6C7 position as a key reaction.

  在C中的未识别的配置5和C 10在callystatin A（1），从海洋海绵一个有效的细胞毒性的聚酮化合物Callyspongia截形，被确定为[R ，- [R通过的圆二色性光谱比较1与两个模型化合物2和3。化合物2和3是通过在C 6 = C 7位置进行E选择性Wittig烯化反应作为关键反应合成的。