(4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane | 169871-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane
• 英文别名: 4-O-；(4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 169871-37-8
• 化学式: C₂₃H₃₀O₄Si
• 分子量: 398.574
• InChiKey: IARLEQVUVIJKBD-NHCUHLMSSA-N

物化性质

• 沸点：
  449.0±43.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 草酰氯 、 双氧水 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (Z)-7-[(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]hept-5-enoic acid
  参考文献：
  名称：

  Synthesis of dl-cis- and (4R,5R)-trans-7-[2,2-dimethyl-4-(phenylsulfonyl)-aminomethyl-1,3-dioxolan-5-yl]-5(Z)-heptenoic acid analogues as platelet thromboxane A2 receptor antagonist

  摘要：

  The title compounds have been synthesized and their in vitro thromboxane A(2) (TxA(2)) receptor antagonist activity evaluated. Both cis and trans isomers (1, 2) were shown to specifically inhibit submaximal human platelet aggregation induced by 225 nM U46619 in a dose-dependent manner with an IC50 of 1 mu M. The concentration of 1 and 2 required to completely block maximal aggregation induced by 3 mu M U46619 was 3 mu(M).

  DOI：

  10.1016/0223-5234(96)88240-7
• 作为产物：
  描述：

  (-)-2,3-O-亚异丙基-D-苏力糖醇 在 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 (4R,5S)-trans-2,2-dimethyl-4-tert-butyldiphenylsiloxymethyl-5-formyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of dl-cis- and (4R,5R)-trans-7-[2,2-dimethyl-4-(phenylsulfonyl)-aminomethyl-1,3-dioxolan-5-yl]-5(Z)-heptenoic acid analogues as platelet thromboxane A2 receptor antagonist

  摘要：

  The title compounds have been synthesized and their in vitro thromboxane A(2) (TxA(2)) receptor antagonist activity evaluated. Both cis and trans isomers (1, 2) were shown to specifically inhibit submaximal human platelet aggregation induced by 225 nM U46619 in a dose-dependent manner with an IC50 of 1 mu M. The concentration of 1 and 2 required to completely block maximal aggregation induced by 3 mu M U46619 was 3 mu(M).

  DOI：

  10.1016/0223-5234(96)88240-7

文献信息

• Synthesis of Glycocinnasperimicin D
  作者：Taihei Nishiyama、Yoshifumi Kusumoto、Ken Okumura、Kanako Hara、Shohei Kusaba、Keiko Hirata、Yukihiro Kamiya、Minoru Isobe、Keiji Nakano、Hiyoshizo Kotsuki、Yoshiyasu Ichikawa

  DOI：10.1002/chem.200901745

  日期：2010.1.11

  The first total synthesis of amino sugar antibiotic glycocinnasperimicin D (1) has been achieved by a convergent, three‐component coupling strategy. The key steps involve the Heck–Mizoroki reaction by using the iodophenyl glycoside 50 and acryl amide 32 to furnish the right core structure of 1, and the construction of the urea glycoside employing the reaction of glycosyl isocyanate 8 with amino sugar

  氨基糖抗生素糖皮质激素亚胺D（1）的第一个全合成方法是通过收敛的三组分偶联策略实现的。的关键步骤涉及通过使用碘苯基糖苷赫克-Mizoroki反应50和丙烯酰胺32，得到的右侧芯结构1，并采用糖基异氰酸酯的反应的尿素糖苷的结构8与氨基糖9。通过氧化异腈10制备异氰酸糖基酯8，在偶联事件中显示出极好的反应性。在合成过程中遇到的合成障碍导致了使用2-氨基-六吡喃糖的α-选择性路易斯酸催化的苯基糖基化过程的发展，以及一种不影响甲硅烷基醚的乙酰胺脱保护的方法。
• Synthesis of the C(43)−C(67) Fragment of Amphidinol 3
  作者：Jacqueline D. Hicks、Eric M. Flamme、William R. Roush

  DOI：10.1021/ol052322j

  日期：2005.11.1

  [reaction: see text] A synthesis of the C(43)-C(67) fragment of amphidinol 3 (AM3) has been accomplished by a route that features the use of a double allylboration reaction for synthesis of 1,5-diol 4b, which serves as a precursor to dihydropyran 11.

  [反应：参见正文]通过以使用双烯丙基硼化反应合成1,5-二醇4b为特征的途径，完成了香豆酚3（AM3）C（43）-C（67）片段的合成，它是二氢吡喃11的前体。
• Synthesis of Highly Functionalized Enantiopure Halocyclopropanes Derived from Carbohydrates
  作者：Humberto Rodríguez-Solla、Carmen Concellón、Vicente del Amo、Ainhoa Díaz-Pardo、Elena G. Blanco、Santiago García-Granda、M. Rosario Díaz、Ricardo Llavona、Raquel G. Soengas

  DOI：10.1002/ejoc.201300322

  日期：2013.8

  The authors acknowledge financial support from the Spanish Ministerio de Economia y Competitividad (MINECO) (grant numbers CTQ2010-14959, MAT2006-01997, MAT2010-15094 and Factoria de Cristalizacion Consolider Ingenio 2010), the Portuguese Fundacao para a Ciencia e a Tecnologia (FCT), the European Union (EU), Quadro de Referencia Estrategico Nacional (QREN), Fundo Europeu de Desenvolvimento Regional

  作者感谢西班牙政府经济与竞争部长 (MINECO)（赠款编号 CTQ2010-14959、MAT2006-01997、MAT2010-15094 和 Factoria de Cristalizacion Consolider Ingenio 2010）、葡萄牙基金（Cristalizacion Consolider Ingenio 2010）的财政支持, 欧盟 (EU), Quadro de Referencia Estrategico Nacional (QREN), Fundo Europeu de Desenvolvimento Regional (FEDER) 和 Programa Operacional Tematico Factores de Competitividade (COMPETE)（项目 PEst-C/QUI/UI0062/2011）。CC 和 V. d. A. 感谢部长级
• Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium
  作者：Humberto Rodríguez-Solla、Raquel Soengas、Noemí Alvaredo

  DOI：10.1055/s-0031-1290441

  日期：2012.9

  We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.
• Stereoselective Synthesis of Carbohydrate-Derived N-Sulfonyl Aziridines
  作者：Humberto Rodríguez-Solla、Carmen Concellón、Noemí Alvaredo、Ricardo Llavona、Santiago García-Granda、M. Díaz、Raquel Soengas

  DOI：10.1055/s-0032-1317954

  日期：——

  A novel reaction of iodomethyllithium with a variety of sugar-derived N-sulfinyl imines, under very mild conditions, is described. N-Sulfonyl aziridines were easily obtained in high yields and in moderate to good stereoselectivities through an addition/oxidation protocol. A mechanism is proposed that is supported by the results of X-ray diffraction studies.