(R)-<2<(Methanesulfonyl)oxy>ethyl>oxirane | 41241-10-5

• 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: (R)-<2<(Methanesulfonyl)oxy>ethyl>oxirane
• 英文别名: (R)-(2-hydroxyethyl)oxyrane methanesulfonate；(2R)-4-methanesulfonyloxy-1,2-epoxybutane；(R)-2-(oxiran-2-yl)ethyl methanesulfonate；(R)-(2-methanesulfonyloxyethyl)oxirane；2-(Oxiran-2-yl)ethyl methanesulfonate
• CAS: 41241-10-5
• 化学式: C₅H₁₀O₄S
• 分子量: 166.198
• InChiKey: BJQOPANNIMUHEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-<2<(Methanesulfonyl)oxy>ethyl>oxirane 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 以81%的产率得到(S)-(-)-4-iodo-1,2-epoxybutane
  参考文献：
  名称：

  Preparation of (R)-(+)- and (S)-(-)-4-iodo-1,2-epoxybutane [(R)- and (S)-(2-iodoethyl)oxirane], useful chiral synthons

  摘要：

  DOI：

  10.1021/jo00319a034
• 作为产物：
  描述：

  2(S)-(tetrahydropyranyloxy)-1,4-bis((methylsulfonyl)oxy)butane 在 甲烷磺酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 11.0h， 生成 (R)-<2<(Methanesulfonyl)oxy>ethyl>oxirane
  参考文献：
  名称：

  Preparation of (R)-(+)- and (S)-(-)-4-iodo-1,2-epoxybutane [(R)- and (S)-(2-iodoethyl)oxirane], useful chiral synthons

  摘要：

  DOI：

  10.1021/jo00319a034

文献信息

• 2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R,6S)-6-(1(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem antibacterial
  作者：Robert A. Volkmann、Paul R. Kelbaugh、Deane M. Nason、V. John Jasys

  DOI：10.1021/jo00042a010

  日期：1992.7

  A practical synthesis of potent penem antibacterials, CP-70,429 (1) (sulopenem) and CP-81,054 (2), is described. (L)-Aspartic acid was utilized to generate both the (3S)- and (3R)-thiolanylthio side chains of (5R,6S)-6-(1-(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem-3-carboxylic acids 1 and 2. This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19. To accommodate the fragile side chain sulfoxide moiety of the targeted beta-lactams, standard penem synthetic methodology was modified to facilitate the conversion of 15 and 19 to 1 and 2. The reactive chloroazetidinone 4b was utilized to generate key azetidinone trithiocarbonate intermediate 22 which contains the requisite penem side chain. A chemoselective oxalofluoride-based azetidinone N-acylation procedure, which avoids sulfoxide O-acylation, was required for the conversion of 22 to the penem framework.
• Synthesis of chiral phosphoantigens and their activity in γδ T cell stimulation
  作者：Yongcheng Song、Yonghui Zhang、Hong Wang、Amy Raker、John Sanders、Erin Broderick、Allen Clark、Craig Morita、Eric Oldfield

  DOI：10.1016/j.bmcl.2004.06.052

  日期：2004.9

  gammadelta T cells expressing Vgamma2Vdelta2 T cell receptors are activated by a broad range of phosphorus-containing small molecules, termed phosphoantigens, and are of interest in the context of the chemotherapy of B cell malignancies. Here, we report the synthesis of four pairs of chiral phosphoantigens: the bromohydrins of isopentenyl diphosphate (Phosphostim(TM)), the epoxides of isopentenyl diphosphate (EIPP); and the corresponding bromohydrin and epoxide analogs of but-3-enyl diphosphate. The ability of each compound to stimulate human Vgamma2Vdelta2 T cells was determined by TNF-alpha release and cell proliferation. In these assays, the (R)-bromohydrin diphosphates were, on average, about twice as active as the (S)-bromohydrin diphosphates. In contrast, the (S)-form of EIPP was about twice as active as (R)-EIPP. The activities of the epoxy but-3-enyl diphosphates were both very low. These results suggest that chiral phosphoantigens, as opposed to racemic mixtures, may have utility in immunotherapy. (C) 2004 Elsevier Ltd. All rights reserved.
• Shibata, Tomoyuki; Iino, Kimio; Sugimura, Yukio, Heterocycles, 1986, vol. 24, # 5, p. 1331 - 1346
  作者：Shibata, Tomoyuki、Iino, Kimio、Sugimura, Yukio

  DOI：——

  日期：——
• Preparation of (R)-(+)- and (S)-(-)-4-iodo-1,2-epoxybutane [(R)- and (S)-(2-iodoethyl)oxirane], useful chiral synthons
  作者：Dale L. Boger、James S. Panek

  DOI：10.1021/jo00319a034

  日期：1981.3