1-(tert-butyldimethylsilyloxy)-2-methyl-buten-4-ol | 257612-06-9

• 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: 1-(tert-butyldimethylsilyloxy)-2-methyl-buten-4-ol
• 英文别名: (Z)-4-(tert-butyldimethylsilanyloxy)-3-methyl-but-2-en-1-ol；(Z)-4-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-en-1-ol
• CAS: 257612-06-9
• 化学式: C₁₁H₂₄O₂Si
• 分子量: 216.396
• InChiKey: DAEPLOLXVLUEEE-YFHOEESVSA-N

物化性质

• 沸点：
  257.3±28.0 °C(predicted)
• 密度：
  0.889±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  1-(tert-butyldimethylsilyloxy)-2-methyl-buten-4-ol 在 盐酸 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 modified AD-mix β 、 水 、 碳酸氢钠 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 40.0h， 生成 (2R,3S)-2,3,4-三羟基-3-甲基丁基磷酸二氢酯
  参考文献：
  名称：

  Synthesis of 2-C-Methyl-d-erythritol 4-Phosphate:  The First Pathway-Specific Intermediate in the Methylerythritol Phosphate Route to Isoprenoids

  摘要：

  2-C-Methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2 propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.

  DOI：

  10.1021/ol991299x
• 作为产物：
  描述：

  叔丁基二甲基(2-丙炔氧基)硅烷 在 正丁基锂 、 copper bromide dimethyl sulfide complex 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-(tert-butyldimethylsilyloxy)-2-methyl-buten-4-ol
  参考文献：
  名称：

  Synthesis of 2-C-Methyl-d-erythritol 4-Phosphate:  The First Pathway-Specific Intermediate in the Methylerythritol Phosphate Route to Isoprenoids

  摘要：

  2-C-Methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2 propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.

  DOI：

  10.1021/ol991299x

文献信息

• Synthesis of Novel Tetrahydroisoquinoline CXCR4 Antagonists with Rigidified Side-Chains
  作者：Edgars Jecs、Eric J. Miller、Robert J. Wilson、Huy H. Nguyen、Yesim A. Tahirovic、Brook M. Katzman、Valarie M. Truax、Michelle B. Kim、Katie M. Kuo、Tao Wang、Chi S. Sum、Mary E. Cvijic、Gretchen M. Schroeder、Lawrence J. Wilson、Dennis C. Liotta

  DOI：10.1021/acsmedchemlett.7b00406

  日期：2018.2.8

  potent TIQ15-derived CXCR4 antagonists is reported. In this investigation, the TIQ15 side-chain was constrained to improve its drug properties. The cyclohexylamino congener 15a was found to be a potent CXCR4 inhibitor (IC50 = 33 nM in CXCL12-mediated Ca2+ flux) with enhanced stability in liver microsomes and reduced inhibition of CYP450 (2D6). The improved CXCR4 antagonist 15a has potential therapeutic

  报道了有效的TIQ15衍生的CXCR4拮抗剂的结构活性关系研究。在这项研究中，TIQ15侧链被限制以改善其药物特性。发现环己基氨基同源物15a是有效的CXCR4抑制剂（在CXCL12介导的Ca 2+通量中IC 50 = 33 nM ），在肝微粒体中的稳定性增强，并且对CYP450（2D6）的抑制作用降低。改进的CXCR4拮抗剂15a具有作为单药或联合抗癌疗法的潜在治疗应用。
• Synthesis of Novel Difluoro-Cyclopropyl Guanine Nucleosides and Their Phosphonate Analogues as Potent Antiviral Agents
  作者：Hua Li、Jin Cheol Yoo、Eunae Kim、Joon Hee Hong

  DOI：10.1080/15257770.2011.625374

  日期：2011.11

  The synthesis of new rigid guanine analogues with anti-HIV-1 and anti-herpes viral activities is described. The phosphonate of difluorocyclopropane nucleoside analogue 26 exhibits in vitro anti-HIV-1 activity similar to that of PMEA in MT-4 cells. Further, analogue 20 shows moderate anti-HCMV activity in MRC cells.

  描述了具有抗HIV-1和抗疱疹病毒活性的新型刚性鸟嘌呤类似物的合成。二氟环丙烷核苷类似物26的膦酸酯具有类似于MT-4细胞中PMEA的体外抗HIV-1活性。此外，类似物20在MRC细胞中显示出中等的抗HCMV活性。
• Total Synthesis of (−)-Jiadifenin
  作者：Yang Yang、Xingnian Fu、Jianwei Chen、Hongbin Zhai

  DOI：10.1002/anie.201203176

  日期：2012.9.24

  As easy as ABCD: (-)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4'-bromo-2'-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland-Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson-Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.
• Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from <i>Agrobacterium tumefaciens</i>
  作者：Sergiy G. Krasutsky、Marek Urbansky、Chad E. Davis、Christian Lherbet、Robert M. Coates、C. Dale Poulter

  DOI：10.1021/jo501529k

  日期：2014.10.3

  The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where it intersects with the mevalonate pathway found in some Bacteria, Archaea, and Eukarya, including the cytosol of plants. D-3-Methylerythritol-4-phosphate (MEP), the first pathway-specific intermediate in the pathway, is converted to IPP and DMAPP by the consecutive action of the IspD-H proteins. We synthesized five D-MEP analogues-D-erythritol-4-phosphate (EP), D-3-methylthrietol-4-phosphate (MTP), D-3-ethylerythritol-4-phosphate (EEP), D-1-amino-3-methylerythritol-4-phosphate (NMEP), and D-3-methylerythritol-4-thiolophosphate (MESP)-and studied their ability to function as alternative substrates for the reactions catalyzed by the IspDF fusion and IspE proteins from Agrobacterium tumefaciens, which covert MEP to the corresponding eight-membered cyclic diphosphate. All of the analogues, except MTP, and their products were substrates for the three consecutive enzymes.
• Synthesis of 2-<i>C</i>-Methyl-<scp>d</scp>-erythritol 4-Phosphate:  The First Pathway-Specific Intermediate in the Methylerythritol Phosphate Route to Isoprenoids
  作者：Andrew T. Koppisch、Brian S. J. Blagg、C. Dale Poulter

  DOI：10.1021/ol991299x

  日期：2000.1.1

  2-C-Methyl-D-erythritol 4-phosphate (4), formed from 1-deoxy-D-xylulose 5-phosphate (3), is the first pathway-specific intermediate in the methylerythritol phosphate route for the biosynthesis of isoprenoid compounds in bacteria, algae, and plant chloroplasts. In this report, 4 was synthesized from 1,2 propanediol (7) in seven steps with an overall yield of 32% and in an enantiomeric excess of 78%.