2′-propyn-1′-yl-4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 158053-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2′-propyn-1′-yl-4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: (6S,2R,3R)-2-methylcarbonyloxymethyl-6-(2-propynyloxy)-3,6-dihydro-2H-3-pyranyl acetate；2'-propyn-1'-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside；prop-2-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside；[(2R,3R,6S)-3-acetyloxy-6-prop-2-ynoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 158053-95-3
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: IUPPZLJWDOLLRS-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-叠氮基-2-(呋喃-2-基)乙醇 、 2′-propyn-1′-yl-4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 [(2R,3R,6S)-3-acetyloxy-6-[[1-[(1S)-1-(furan-2-yl)-2-hydroxyethyl]triazol-4-yl]methoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  Multicomponent Cascade Transformation of d-Glucal to Furan-Appended Triazole Glycoconjugates

  摘要：

  Novel one-pot three- and four-component transformations of D-glucal to furan-based hydroxy triazole glycoconjugates have been achieved by sequential addition of reagents in the presence of Cu(OTf)(2)-Cu powder as catalysts. In general the carbohydrate-derived products were formed with high diastereomeric purity.

  DOI：

  10.1021/jo100475e
• 作为产物：
  描述：

  2-丙炔-1-醇 、 D-三乙酰半乳糖烯 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以76%的产率得到2′-propyn-1′-yl-4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  铜（ii）催化的立体式1,2加成与“武装”和“解除武装”的糖供体的Ferrier糖基化作用。

  摘要：

  通过使用Cu（II）-催化剂作为启动子，实现了“武装”和“解除武装”的糖基供体的选择性激活，从而实现了立体控制的糖基化。在该方法中独特的立体化学结果主要受供体和所用溶剂体系上存在各种保护基的影响。该方案可与多种糖苷配基（包括碳水化合物，氨基酸和天然产物）兼容，以高α-异头异构体选择性获得脱氧糖苷和糖缀合物。值得注意的是，该方法的合成实用性已被充分验证用于包含2-脱氧成分的三糖的立体选择性组装。涉及氘代实验的机理研究验证了合成-在武装供体的双键上进行非对映体选择性的1,2-加成受体。

  DOI：

  10.1039/d0ob01042a

文献信息

• Synthesis of 2,3-Unsaturated Alkynyl O-Glucosides from Tri-O-acetyl-d-glucal by Using Montmorillonite K-10/Iron(III) Chloride Hexahydrate with Subsequent Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition
  作者：Ronaldo de Oliveira、Valentina Melo、Willyenne Dantas、Celso Camara

  DOI：10.1055/s-0034-1378829

  日期：——

  within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H-triazolyl O-glucoside derivatives through a click reaction. Two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O-acetyl-d-glucal and triazole alcohols

  摘要 考虑了两种合成2，3-不饱和O-葡萄糖基-1,2,3-三唑的策略。三-之间的第一，涉及反应ö乙酰基d -glucal和三唑醇没有给出立体选择性。第二种策略是通过Ferrier重排从糖和炔醇中提供2,3-不饱和的O-糖苷。该方法在二氯甲烷中使用掺有六水合氯化铁（III）的蒙脱石K-10，可在短时间内以高至优异的产率和高α-立体选择性提供新的糖苷。随后，将糖苷与2-叠氮基-1,4-萘醌偶联以生成新的1,2,3-1 H-三唑基O系列-葡萄糖苷衍生物通过点击反应。 考虑了两种合成2，3-不饱和O-葡萄糖基-1,2,3-三唑的策略。三-之间的第一，涉及反应ö乙酰基d -glucal和三唑醇没有给出立体选择性。第二种策略是通过Ferrier重排从糖和炔醇中提供2,3-不饱和的O-糖苷。该方法在二氯甲烷中使用掺有六水合氯化铁（III）的蒙脱石K-10，可在短时间内以高至优异的产率和高α-立体选择性
• Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C₆F₅)₃ as Catalyst
  作者：Abhijit Sau、Carlos Palo-Nieto、M. Carmen Galan

  DOI：10.1021/acs.joc.8b02613

  日期：2019.3.1

  α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α- O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile

  B（C6F5）3使无金属的空前的基质控制的从糖类中脱氧糖苷的直接α-立体选择性合成成为可能。在催化剂存在下，在75°C下用失活的糖类获得2,3-不饱和α-O-糖苷产物，而使用在较低温度下C-3上不带有离去基团的活化的糖类形成2-脱氧糖苷。通过硼供体的糖基供体和亲核体受体的活化，该反应以良好的收率很好地进行。该方法以一系列稀有和生物学上相关的糖苷类似物的合成为例。
• Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols
  作者：D. Bradley G. Williams、Sandile B. Simelane、Henok H. Kinfe

  DOI：10.1039/c2ob25540e

  日期：——

  A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

  提出了在Al（OTf）3催化的醇直接添加或某些糖基中的Ferrier重排反应之间的温度控制机制切换。研究了范围和局限性以及糖基上保护基的立体化学和性质的影响。
• Microwave-Induced, InCl₃-CatalyzedFerrier Rearrangement of Acetyl­glycals: Synthesis of 2,3-UnsaturatedGlycopyranosides
  作者：Saibal Kumar Das、K. Anantha Reddy、Joyita Roy

  DOI：10.1055/s-2003-40991

  日期：——

  Indium(III) chloride catalyzed, microwave assisted Ferrier rearrangementon different per-O-acetylglycals leadsto an efficient synthesis of 2,3-unsaturated O-glycosidesin good to excellent yields.

  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。
• Niobium(V) chloride catalyzed microwave assisted synthesis of 2,3-unsaturated O-glycosides by the Ferrier reaction
  作者：Srinivas Hotha、Ashish Tripathi

  DOI：10.1016/j.tetlet.2005.05.015

  日期：2005.7

  NbCl5 catalyzes the Ferrier reaction of per-O-acetylated glycals with primary, secondary, allylic, benzylic and monosaccharide alcohols to give 2,3-unsaturated α-glycosides in short reaction times under microwave irradiation conditions.

  NbCl 5催化过-O-乙酰化的糖与伯，仲，烯丙基，苄基和单糖醇的Ferrier反应，在微波辐射条件下，在较短的反应时间内即可生成2,3-不饱和的α-糖苷。