pent-4-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 1173831-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: pent-4-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-pent-4-ynoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1173831-41-8
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: WZHCLPOHMBTYKD-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  pent-4-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以78%的产率得到[(2R,3S,6S)-3-acetyloxy-6-[10-[[(2R,3S,6S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxy]deca-4,6-diynoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system

  摘要：

  A simple copper promoting system CuI/NBS/DIPEA was first found to efficiently promote Glaser coupling reaction under ambient temperature. The alkynes with sensitive groups such as acetal and ketal, TBDMS, ester and amide could react smoothly to afford the functionalized 1,3-diynes under the CuI/NBS/DIPEA promoting system in good yields. And the successful application of the Cul/NBS/DIPEA promoting system in sugar and amino acid-building blocks indicated the potential of this method in the construction of designed sugar and peptide biomolecules. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.04.065
• 作为产物：
  描述：

  4-戊炔-1-醇 、 乙酰化葡萄烯糖 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到pent-4-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Convertible Formation of Different Glycoside Using Molecular Iodine

  摘要：

  The observation of convertible formation between 2-deoxy-2-iodo-O-glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation.

  DOI：

  10.3987/com-10-12043

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
• Stereoselective synthesis and antitumoral activity of Z-enyne pseudoglycosides
  作者：Claudio R. Dantas、Jucleiton J. R. de Freitas、Queila P. S. Barbosa、Gardenia C. G. Militão、Thiago D. S. Silva、Teresinha G. da Silva、Antônio A. S. Paulino、Juliano C. R. Freitas、Roberta A. Oliveira、Paulo H. Menezes

  DOI：10.1039/c6ob00945j

  日期：——

  An efficient approach for the synthesis of Z-1,3-enynes based on the coupling reaction of Z-vinyl tellurides and alkynes containing a pseudoglycoside moiety is described. The products were obtained in good yields via a stereoselective way. Preliminary screening against three tumor cell lines indicated that the synthesized compounds are promising intermediates for the synthesis of an array of more potent

  描述了基于Z-乙烯基碲化物和含有假糖苷部分的炔烃的偶联反应合成Z -1，3-烯炔的有效方法。通过立体选择的方法以高收率获得了产物。对三种肿瘤细胞系的初步筛选表明，合成的化合物是合成更有力的靶结构阵列的有前途的中间体。