1-O-tert-butyldimethylsilyloxy-3-O-methanesulfonyloxy-propane | 257286-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-O-tert-butyldimethylsilyloxy-3-O-methanesulfonyloxy-propane
• 英文别名: 3-((tert-butyldimethylsilyl)oxy)propyl methanesulfonate；3-t-butyldimethylsilyloxy propyl mesylate；1-Propanol,3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-,methanesulfonate；3-[tert-butyl(dimethyl)silyl]oxypropyl methanesulfonate
• CAS: 257286-40-1
• 化学式: C₁₀H₂₄O₄SSi
• 分子量: 268.45
• InChiKey: JGSNTYKNXHWBBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldimethylsilyloxy-3-O-methanesulfonyloxy-propane 生成 [1α,2β,3β(1E,3R),4α]-3-[[3-(3-Hydroxy-4,4-dimethyl-1-octenyl)-7-oxabicyclo[2.2.1]hept-2-yl]methoxy]propionic acid
  参考文献：
  名称：

  7-Oxabicycloheptane ethers useful in the treatment of thrombolytic

  摘要：

  提供了具有以下结构式的前列腺素类7-氧杂双环庚烷醚衍生物，包括其所有立体异构体。这些化合物是心血管药物，例如，可用于治疗溶栓性疾病。

  公开号：

  US04513103A1
• 作为产物：
  描述：

  3-(叔丁基二甲基硅氧)丙醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到1-O-tert-butyldimethylsilyloxy-3-O-methanesulfonyloxy-propane
  参考文献：
  名称：

  [EN] LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS
  [FR] LIPIDES ET COMPOSITIONS LIPIDIQUES PERMETTANT L'ADMINISTRATION DE PRINCIPES ACTIFS

  摘要：

  这项发明提供了一个式（I）的化合物，或者其药学上可接受的盐，其中RA、RB、R2和R4在此处定义。式（I）的化合物及其药学上可接受的盐是阳离子脂质，可用于将生物活性物质传递给细胞和组织。

  公开号：

  WO2016037053A1

文献信息

• Remarkable template effect of a Lewis acid receptor in the intramolecular radical cyclization: control of reaction pathway as well as stereochemistry
  作者：Takashi Ooi、Yasutoshi Hokke、Eiji Tayama、Keiji Maruoka

  DOI：10.1016/s0040-4020(00)01007-3

  日期：2001.1

  Abstract A remarkable template effect in the intramolecular radical cyclization process has been observed by the successful utilization of Lewis acid receptor, aluminum tris(2,6-diphenylphenoxide) (ATPH). The origin of this efficient template effect by ATPH would be ascribable to the well-defined reaction environment created in front of the aluminum coordination center; this enables appropriate proximity

  摘要 通过路易斯酸受体三(2,6-二苯酚)铝(ATPH)的成功利用，观察到分子内自由基环化过程中的显着模板效应。ATPH 产生的这种有效模板效应可归因于在铝配位中心前创造的明确的反应环境；这使得初始产生的碳自由基与过渡态的不饱和碳-碳键适当接近，以实现平滑环化，因此完全抑制了不希望的分子间还原途径。此外，ATPH 独特的空腔提供的这种构象限制改变了环化的立体选择性。
• Constrained H-Type 2 Blood Group Trisaccharide Synthesized in a Bioactive Conformation via Intramolecular Glycosylation
  作者：Shirley A. Wacowich-Sgarbi、David R. Bundle

  DOI：10.1021/jo990979a

  日期：1999.12.1

  The methyl glycoside of the II-type 2 trisaccharide 1 was synthesized in a constrained, bioactive conformation via intramolecular aglycon delivery. Computer modeling of the crystal structure of the Ulex europaeus I lectin with a docked H-type 2 trisaccharide suggested that the disaccharide Galp(1-->4)GlcpNAc1-->OCH3 could be tethered in a bioactive conformation if Gal O-6 and GlcNAc O-3 are linked via a three-carbon tether. The ethyl 1-thiogalactopyranoside 13 was used to alkylate the methyl 2-acetamido-2-deoxy glucopyranoside 7, and the resulting dimer was subjected to intramolecular glycosylation following protecting group manipulation. The tethered disaccharide 4 was glycosylated by the activated fucopyranosyl donor 3 to give the protected target molecule 17. Solid-phase binding assays showed that the tethered trisaccharide 2 was 3-fold less active than native II-type 2 trisaccharide 1 when assayed against the U, europaeus I lectin, whereas it was 250 times less active when assayed with the Psophocarpus tetragonolobus II lectin. The observed activities are consistent with published models for H-trisaccharide interactions with Ulex: and Psophocarpus lectins and provide further evidence that suggests reduction of oligosaccharide flexibility by intramolecular tethering provides no significant gain in binding energy.