(3R,5S)-5-methyl-3-phenyl-1,2-oxathiolane 2,2-dioxide | 688801-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: (3R,5S)-5-methyl-3-phenyl-1,2-oxathiolane 2,2-dioxide
• 英文别名: (3R,5S)-5-methyl-3-phenyloxathiolane 2,2-dioxide
• CAS: 688801-46-9
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: KDGYKVSZCSEMCW-WCBMZHEXSA-N

物化性质

• 沸点：
  390.0±31.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-methyl-3-phenyl-1,2-oxathiolane 2,2-dioxide 以 乙醚 为溶剂， 反应 72.0h， 生成 (1R,3R)-methyl 3-methoxy-1-phenylbutane-1-sulfonate
  参考文献：
  名称：

  Enders, Dieter; Harnying, Wacharee, Arkivoc, 2004, vol. 2004, # 2, p. 181 - 188

  摘要：

  DOI：
• 作为产物：
  描述：

  苄磺酰氯 在 palladium diacetate 正丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 121.0h， 生成 (3R,5S)-5-methyl-3-phenyl-1,2-oxathiolane 2,2-dioxide
  参考文献：
  名称：

  Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates

  摘要：

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.046

文献信息

• A Highly Efficient Asymmetric Synthesis of Homotaurine Derivatives via Diastereoselective Ring-Opening of γ-Sultones
  作者：Dieter Enders、Wacharee Harnying

  DOI：10.1055/s-2004-831256

  日期：——

  A highly efficient asymmetric synthesis of α,γ-substituted γ-amino sulfonates via diastereoselective ring-opening of enantiopure α,γ-substituted γ-sultones with inversion of configuration at the attacked γ-carbon is described. In the key step sodium azide is used as the nucleophilic nitrogen source. Secondary and tertiary γ-amino sulfonates were synthesized in very good yields and excellent diastereo- and enantiomeric excesses (de, ee ≥98%).

  描述了一种高效的不对称合成α,γ-取代的γ-氨基磺酸酯的方法，该方法通过对手性纯的α,γ-取代的γ-硫内酯进行选择性开环，在攻击的γ-碳处反转构型。在关键步骤中使用了叠氮化钠作为核亲和氮源。合成的次级和三级γ-氨基磺酸酯具有非常好的产率和优异的非对映体和对映体过量（de, ee ≥98%）。
• A Practical Approach Towards the Asymmetric Synthesis of α,γ-Substituted γ-Sultones
  作者：Dieter Enders、Wacharee Harnying、Nicola Vignola

  DOI：10.1055/s-2002-34229

  日期：——

  The first auxiliary controlled synthesis of enantiopure α,γ-substituted γ-sultones via α-allylated chiral sulfonates is described. The high asymmetric inductions of the α-allylations were reached with our previously described auxiliary 1,2:5,6-di-O-isopropylidene-α-d-allofuranose (de≥98%). Cleavage of the auxiliary and successive diastereoselective ring closure of the sulfonic acid intermediates led to the title compounds in high selectivities (de, ee≥98%) and good to excellent yields (52-90%). Enantiopure α,γ-substituted γ-sultones are interesting intermediates in the reaction with various nucleophiles.

  本文描述了通过α-烯丙基化手性磺酸盐对对映纯的α,γ-取代的γ-琥珀酸内酯进行首次辅助控制合成。通过我们之前描述的辅助1,2:5,6-二-O-异亚丙基-α-d-呋喃糖（de≥98%），实现了α-烯丙基化的高不对称诱导。辅助剂的裂解和磺酸中间体的连续非对映选择性环闭合，以高选择性（de, ee≥98%）和良好至极佳的产率（52-90%）获得了标题化合物。对映纯的α,γ-取代的γ-琥珀酸内酯是与各种亲核试剂反应的有趣中间体。
• Asymmetric Synthesis ofα,γ-Substitutedγ-Sultones via Allylation of Chiral Lithiated Sulfonates
  作者：Dieter Enders、Wacharee Harnying、Nicola Vignola

  DOI：10.1002/ejoc.200300342

  日期：2003.10

  The first auxiliary controlled asymmetric synthesis of enantiopure α,γ-substituted γ-sultones via α-allylation of lithiated sulfonates by using 1,2:5,6-di-O-isopropylidene-α-D-allofuranose as chiral auxiliary is described. The high asymmetric inductions of the α-allylations were reached in good to excellent yields. Successive epimerization-free cleavage of the auxiliary and diastereoselective ring

  描述了使用 1,2:5,6-二-O-异亚丙基-α-D-别呋喃糖作为手性助剂，通过锂化磺酸盐的 α-烯丙基化，控制对映体纯 α,γ-取代 γ-磺内酯的第一个辅助控制不对称合成。α-烯丙基化的高不对称诱导达到了良好至极好的产率。在一锅法中，磺酸中间体的辅助和非对映选择性闭环的连续无差向异构化裂解导致标题化合物的产率良好至极好以及非对映体和对映体过量（de，ee ≥ 98％）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Diastereoselective Hydrolysis of α,γ-Substituted γ-Sultones in the Asymmetric Synthesis of γ-Hydroxy Sulfonates
  作者：Dieter Enders、Wacharee Harnying、Gerhard Raabe

  DOI：10.1055/s-2004-815952

  日期：——

  The hydrolysis of enantiopure α,γ-substituted γ-sultones with water under mild conditions leads to α,γ-substituted γ-hydroxy methyl sulfonates in very good yields and excellent diastereo- and enantiomeric excesses (de, ee ≥ 98%). The reaction proceeds via a SN2 mechanism with inversion of configuration at the attacked γ-carbon atom whose absolute configuration was established by X-ray crystallography.

  在温和的条件下用水水解对映体纯的δ±,δ³-取代的δ³-磺酮，可以得到δ±,δ³-取代的δ³-羟基甲基磺酸盐，收率非常高，非对映和对映体过量率非常好（de, ee ≥ 98%）。该反应通过 SN2 机制进行，在被攻击的 δ³ 碳原子上发生构型反转，其绝对构型由 X 射线晶体学确定。