4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-threo-hex-2-enitol | 318959-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-threo-hex-2-enitol
• 英文别名: ((2R,3R)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate；1,3-di-O-acetyl-2,6-anhydro-4,5-dideoxy-D-threo-hex-4-enitol；[(2R,3R)-3-acetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 318959-97-6
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: XICQRHJROALDID-NXEZZACHSA-N

物化性质

• 沸点：
  285.3±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-threo-hex-2-enitol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 29.5h， 生成 (2R,3R)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl oleate
  参考文献：
  名称：

  Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity

  摘要：

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). Here, in order to increase potency and receptor selectivity, we designed and synthesized LysoPS analogues containing the conformational constraints of the glycerol moiety. These reduced structural flexibility by fixation of the glycerol framework of LysoPS using a 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton, and related structures identified compounds which exhibited high potency and selectivity for activation of GPR34 or P2Y10. Morphing of the structural shape of the 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton into a planar benzene ring enhanced the P2Y10 activation potentcy rather than the GPR34 activation.

  DOI：

  10.1021/acs.jmedchem.5b01925
• 作为产物：
  描述：

  [3(2S,4R),4S]-3-(2-allyloxy-3-hydroxyhex-4-enoyl)-4-benzyloxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Grubbs catalyst first generation 、 lithium chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-D-threo-hex-2-enitol
  参考文献：
  名称：

  碳环核苷的高效，一般不对称合成：不对称醛醇/环封闭复分解策略的应用。

  摘要：

  已经开发了碳环和己吡喃糖基核苷的一般有效合成方法。该策略结合了三个关键的转变：不对称的醛醇加成物以建立假糖的相对和绝对构型，闭环易位以构建假糖环，以及Trost型钯（0）介导的取代以组装假糖和糖。芳香基。Carbovir，abacavir及其2'-甲基衍生物以及己吡喃糖基核苷类似物已通过该序列制备。

  DOI：

  10.1021/jo005535p

文献信息

• Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals
  作者：Batthula Srinivas、Thurpu Raghavender Reddy、Sudhir Kashyap

  DOI：10.1016/j.carres.2015.01.009

  日期：2015.4

  for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide and heterocycles such as thiophene and furan reacted smoothly with glycals in the presence of catalytic amount of ruthenium trichloride under mild reaction conditions.

  使用氯化钌（III）开发了一种高效且便捷的C-糖基化方法，用于合成2,3-不饱和C-糖苷。在温和的反应条件下，在催化量的三氯化钌存在下，各种亲核试剂（如烯丙基三甲基硅烷，三乙基硅烷，三甲基甲硅烷基氰化物，三甲基甲硅烷基叠氮化物）和杂环（如噻吩和呋喃）与糖类平稳地反应。
• Efficient Pseudo-enantiomeric Carbohydrate Olefin Ligands
  作者：Holger Grugel、Fabian Albrecht、Tobias Minuth、Mike M. K. Boysen

  DOI：10.1021/ol3015896

  日期：2012.7.20

  pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic

  由d-葡萄糖和d-半乳糖设计了高效的假对映体烯烃配体。这些配体在Rh（I）催化的芳基和烯基硼酸向非手性烯酮的1,4-加成反应中始终产生优异的对映选择性，并具有手性底物的高非对映选择性。与已建立的烯烃配体相反，它们是通过短合成法得到对映体纯的，没有外消旋拆分步骤，这使它们成为具有烯烃供体位点的手性配体的重要补充。
• Methods Of Making Pyranopyrans Such As Pyranopyran Nitrile And Methods of Using Pyranopyrans Such As Pyranopyran Nitrile
  申请人：The United States of America, as Represented by the Secretary of Agriculture

  公开号：US20200093132A1

  公开（公告）日：2020-03-26

  Disclosed herein are methods of making (4aR,6S,8aR)-6-((R)-1-hydroxyethyl)-6,8a-dihydropyrano[3,2-b]pyran-2-(4aH)-one (2) and methods of making (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4). Other pyranopyrans were also synthesized. Also compositions containing (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4) (or other pyranopyrans described herein) and optionally a carrier. In addition, methods for killing microorganisms or weeds on or in an object or area involving contacting the object or area with an effective microorganisms or weeds killing amount of a composition containing (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4) (or other pyranopyrans described herein) and optionally a carrier.

  本发明公开了制备(4aR,6S,8aR)-6-((R)-1-羟乙基)-6,8a-二氢吡喃并[3,2-b]吡喃-2-(4aH)-酮(2)的方法以及制备(4aR,6S,8aR)-6-氰基-6,8a-二氢吡喃并[3,2-b]吡喃-2(4aH)-酮(4)的方法。还合成了其他吡喃并吡喃类化合物。还提供了含有(4aR,6S,8aR)-6-氰基-6,8a-二氢吡喃并[3,2-b]吡喃-2(4aH)-酮(4)（或本文所述的其他吡喃并吡喃类化合物）及可选载体的组合物。此外，还提供了杀灭物体或区域上或内的微生物或杂草的方法，该方法涉及将该物体或区域与含有(4aR,6S,8aR)-6-氰基-6,8a-二氢吡喃并[3,2-b]吡喃-2(4aH)-酮(4)（或本文所述的其他吡喃并吡喃类化合物）及可选载体的组合物接触，该组合物具有有效杀灭微生物或杂草的量。
• A highly stereocontrolled total synthesis of dysiherbaine
  作者：Keisuke Takahashi、Takashi Matsumura、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1039/b709627e

  日期：——

  A total synthesis of dysiherbaine, a potent agonist of AMPA-KA type glutamate receptors, has been accomplished in completely stereocontrolled manner starting from tri-O-acetyl-D-galactal in 25 steps and in 3% overall yield.

  dysiherbaine（一种AMPA-KA型谷氨酸受体的强效激动剂）的总合成已从25个步骤中以三-O-乙酰基-D-半乳糖为起始，以完全立体控制的方式完成，总收率为3％。
• Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction
  作者：Jamie L. Cohen、A. Richard Chamberlin

  DOI：10.1016/j.tetlet.2007.02.016

  日期：2007.4

  intermediate of the dysiherbaine tetrahydropyran core has been achieved in 11 steps and 27% overall yield. The key feature of this synthetic approach is the application of the Donohoe tethered aminohydroxylation reaction to install the amino diol and establish the four contiguous syn stereocenters on the tetrahydropyran ring.

  以11个步骤完成了dysiherbaine四氢吡喃核心高级中间体的立体控制和可扩展合成，总收率达27％。该合成方法的关键特征是应用Donohoe束缚的氨基羟基化反应来安装氨基二醇并在四氢吡喃环上建立四个连续的顺式立体中心。