1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol | 14125-70-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol
• 英文别名: 4,6-O-benzylidine-D-arabino-hex-1-enitol；4,6-O-Benzylidene-D-glucal；4,6-O-benzylidene dihydro-D-glucal；4,6-Benzyliden-1,2-didehydro-1,2-dideoxy-D-arabino-hexopyranose；4,6-O-Benzyliden-D-gulal；(4aR,8R,8aS)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 14125-70-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: XMDUTBYCCVWPLD-FKJOKYEKSA-N

物化性质

• 熔点：
  136-140°C
• 沸点：
  420.9±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 在 吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 33.0h， 生成 4,6-O-benzylidene-3-O-(N-(p-chlorobenzoyloxy)-carbamoyl)-D-glucal
  参考文献：
  名称：

  Osmium-Catalyzed Tethered Aminohydroxylation of Glycals: A Stereodirected Access to 2- and 3-Aminosugars

  摘要：

  The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach. Glucals and galactals showed complementary reactivity in dependence of the stage at which the reaction was performed, i.e., directly or after double-bond shift consequent to a Ferrier rearrangement (that is, on the 1,2 or 2,3-unsaturated sugar), allowing access to both classes of 2-amino (mannosamine) and 3-amino (talosamine) sugar derivatives, respectively.

  DOI：

  10.1021/ol503754f
• 作为产物：
  描述：

  (1R,7R,9R)-5,11-diphenyl-2,4,6,10,12-pentaoxatricyclo[7.4.0.03,7]tridecane 生成 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  HORTON, DEREK;WECKERLE, WOLFGANG, CARBOHYDR. RES., 174,(1988) 305-312

  摘要：

  DOI：

文献信息

• 1,2-<i>trans</i>-Stereoselective Synthesis of <i>C</i>-Glycosides of 2-Deoxy-2-amino-sugars Involving Glycosyl Radicals
  作者：Wen-Ze Shi、Hai Li、Gui-Cai Mu、Ji-Liang Lu、Yuan-Hong Tu、Xiang-Guo Hu

  DOI：10.1021/acs.orglett.1c00551

  日期：2021.4.2

  We report for the first time that the imidate radical can be efficiently added to glycals to generate glycosyl radicals, based on which a general, toxic-reagent-free synthesis of C-glycosides of 2-deoxy-2-amino sugars has been developed. Complementary to previous strategies, the reaction is 1,2-trans-stereoselective and could use aryl alkenes as substrates. The late-stage functionalization and density

  我们首次报道了可以将亚胺酯自由基有效地添加到糖基中以生成糖基自由基，基于此，已经开发了 2-脱氧-2-氨基糖的C-糖苷的通用、无毒试剂合成。作为对先前策略的补充，该反应具有 1,2-反式立体选择性，并且可以使用芳基烯烃作为底物。报告了后期功能化和密度泛函理论计算。
• β-Type Glycosidic Bond Formation by Palladium-Catalyzed Decarboxylative Allylation
  作者：Shaohua Xiang、Zhiqiang Lu、Jingxi He、Kim Le MaiHoang、Jing Zeng、Xue-Wei Liu

  DOI：10.1002/chem.201303241

  日期：2013.10.11

  Decarboxylative allylation of glycals: A β‐type glycosidic bond has been constructed in high regio‐ and stereoselectivity by means of a palladium‐catalyzed decarboxylative O‐glycosylation. Various kinds of glycals with different protecting groups have been examined for this reaction to afford a diverse set of glycosylated products, including phenolic O‐glycosides, thiophenolic S‐glycoside, aliphatic

  糖类的脱羧烯丙基化：通过钯催化的脱羧O糖基化，以高区域和立体选择性构建了β型糖苷键。已对该反应进行了各种具有不同保护基的糖基的检测，以提供各种糖基化产物，包括酚O-糖苷，硫酚S-糖苷，脂族O-糖苷和具有出色的β-选择性和合理至优异的二糖。产量（请参阅计划）。
• Stereospecific C‐Glycosylation by Mizoroki–Heck Reaction: A Powerful and Easy‐to‐Set‐Up Synthetic Tool to Access<i>α</i>‐ and<i>β</i>‐Aryl‐<i>C</i>‐Glycosides
  作者：Thibaud Mabit、Aymeric Siard、Frédéric Legros、Stéphane Guillarme、Arnaud Martel、Jacques Lebreton、François Carreaux、Gilles Dujardin、Sylvain Collet

  DOI：10.1002/chem.201803674

  日期：2018.9.20

  A stereospecific Mizoroki–Heck cross‐coupling of differently substituted glycals with haloarenes resulting in the exclusive formation of either α‐ or β‐aryl‐C‐glycosides depending solely on the configuration at C3 was achieved. The reaction was easy to set up because no specific precautions were required concerning moisture or oxygen, and it proceeded by a chirality transfer from C3 to C1. After optimization

  实现了不同取代的糖基与卤代芳烃的立体特异性Mizoroki-Heck交叉偶联，仅根据C3的构型，导致仅形成α-或β-芳基C-糖苷。该反应易于建立，因为不需要采取任何有关水分或氧气的预防措施，并且通过从C3到C1的手性转移进行反应。在优化交叉偶联条件后，测试了各种制备的乙二醇（7个实例）和芳烃（10个实例），立体定向生成了相应的在C3处带有羰基的芳基C-糖苷，从而为总合成开辟了新的视野糖基化天然产物。
• An approach for disaccharide chiron synthesis using a Ferrier-type rearrangement
  作者：Katarzyna Komor、Wiesław Szeja、Tadeusz Bieg、Nikodem Kuźnik、Gabriela Pastuch-Gawołek、Roman Komor

  DOI：10.1016/j.tetlet.2014.05.025

  日期：2014.7

  We report a new approach for the synthesis of new chiral synthons in which two unsaturated sugars are linked via a glycosidic bond. The di-unsaturated disaccharide can be further functionalized using effective, highly selective methods and used in convergent syntheses of relatively complex glycoconjugates. Our approach utilizes in situ generation of active glycosyl donors via Ferrier-type rearrangement

  我们报告了一种新的手性合成子合成的新方法，其中两个不饱和糖通过糖苷键连接。可以使用有效，高度选择性的方法将二不饱和二糖进一步官能化，并用于相对复杂的糖缀合物的融合合成中。我们的方法利用相转移条件下的Ferrier型重排原位生成活性糖基供体，并随后与亲核试剂反应。
• Stereoselective synthesis of a C-glycosylic compound (a “methyl C-glycoside”) through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination
  作者：Bhagavathy Shanmugasundaram、Babu Varghese、Kalpattu K Balasubramanian

  DOI：10.1016/s0008-6215(02)00137-4

  日期：2002.9

  7-O-benzylidene-1,3,4-trideoxy-D-arabino-hept-3-enitol, a methyl C-glycosylic compound. Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2,6-anhydro-1-deoxyheptose, (a "methyl C-beta-D-glycoside"). The stereochemistry of the 1,2-cyclopropano sugar and the "methyl C-glycoside" were confirmed by single-crystal

  将现成的3,4,6-三-O-乙酰基-D-葡萄糖转化为2,6-脱水-5,7-O-亚苄基-1,3,4-三苯氧基-D-阿拉伯糖-庚-3-烯醇，一种甲基C-糖基化合物。4,6-O-亚苄基-D-葡糖的环丙烷化，然后由三丁基锡烷基自由基介导的1,2-环丙糖的区域选择性开环导致2,6-脱水-1-脱氧庚糖（“甲基C- β-D-糖苷”）。通过单晶X射线衍射研究证实了1，2-环丙糖和“甲基C-糖苷”的立体化学。