(2S,3R)-3,6-dihydro-2-methyl-6-(phenylmethoxy)-3-O-acetyl-2H-pyran-3-ol | 755033-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-3,6-dihydro-2-methyl-6-(phenylmethoxy)-3-O-acetyl-2H-pyran-3-ol
• 英文别名: benzyl 2,3,6-trideoxy-4-O-acetyl-L-erythro-hex-2-enepyranoside
• CAS: 755033-94-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: OAEHQOACVZZMGS-NFCBODTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3,6-dihydro-2-methyl-6-(phenylmethoxy)-3-O-acetyl-2H-pyran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 10.0h， 以85%的产率得到(5R,6S)-5-acetoxy-6-methyltetrahydro-2-pyranol
  参考文献：
  名称：

  A Practical Method for the Stereoselective Generation of β-2-Deoxy Glycosyl Phosphates

  摘要：

  beta-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize beta-2-deoxy sugar phosphates that starts from a-glycosyl chlorides. Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products.

  DOI：

  10.1021/ol049187f
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 、 苯甲醇 在 indium(III) chloride 作用下， 以 乙腈 为溶剂， 反应 0.01h， 以84%的产率得到(2S,3R)-3,6-dihydro-2-methyl-6-(phenylmethoxy)-3-O-acetyl-2H-pyran-3-ol
  参考文献：
  名称：

  Microwave-Induced, InCl₃-CatalyzedFerrier Rearrangement of Acetyl­glycals: Synthesis of 2,3-UnsaturatedGlycopyranosides

  摘要：

  铟(III)氯化物催化的微波辅助Ferrier重排反应对不同的全O-乙酰化糖苷进行了有效合成，得到2,3-不饱和O-糖苷的良好至优异产率。

  DOI：

  10.1055/s-2003-40991

文献信息

• Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach
  作者：Subbarao Yalamanchili、Dina Lloyd、Clay S. Bennett

  DOI：10.1021/acs.orglett.9b01118

  日期：2019.5.17

  The synthesis of the hexasaccharide fragment of landomycin A is reported. Using p-toluenesulfonyl chloride mediated dehydrative glycosylation, we constructed the deoxy-sugar linkages in a stereoselective fashion without the need for temporary prosthetic groups to control selectivity. Through this approach, the hexasaccharide was obtained in 28 steps and 8.9% overall yield, which is an order of magnitude

  报道了土霉素A的六糖片段的合成。使用对甲苯磺酰氯介导的脱水糖基化，我们以立体选择性方式构建了脱氧糖键，而无需使用临时的人工基团来控制选择性。通过这种方法，可以以28个步骤获得六糖，总产率为8.9％，这比以前报道的方法要高一个数量级。
• Direct Synthesis of 2,6‐Dideoxy‐β‐glycosides and β‐Rhamnosides with a Stereodirecting 2‐(Diphenylphosphinoyl)acetyl Group
  作者：Xianglai Liu、Yetong Lin、Wenyi Peng、Zhaolun Zhang、Longwei Gao、Yueer Zhou、Zhe Song、Yingjie Wang、Peng Xu、Biao Yu、Haopeng Sun、Weijia Xie、Wei Li

  DOI：10.1002/anie.202206128

  日期：2022.8.15

  The 2-(diphenylphosphinoyl)acetyl group is highly stereodirecting for the construction of challenging β-configured 2,6-dideoxyglycosides and d/l-rhamnosides. Its synthetic potential was demonstrated in linear or convergent approaches to relevant complex carbohydrates. Variable-temperature NMR studies provided evidence that the reaction proceeds by hydrogen-bond-mediated aglycone delivery.

  2-(二苯基膦酰基)乙酰基具有高度立体定向性，可用于构建具有挑战性的 β-构型 2,6-二脱氧糖苷和d / l-鼠李糖苷。其合成潜力在相关复杂碳水化合物的线性或收敛方法中得到证实。变温 NMR 研究提供了该反应通过氢键介导的糖苷配基递送进行的证据。
• Scope of AuCl3 in the activation of per-O-acetylglycals
  作者：Rengarajan Balamurugan、Srinivasa Rao Koppolu

  DOI：10.1016/j.tet.2009.07.087

  日期：2009.9

  Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.