but-3-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 135195-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: but-3-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-but-3-ynoxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 135195-22-1
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: QDTGRJJAGMLTOT-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  but-3-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 、 水 、 silica gel 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 but-3-en-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies †

  摘要：

  提出了一种催化锡自由基介导的自由基级联反应的一般策略，其中在一步中构建了三个环。三环化过程的初始步骤是使用在1-O和/或4-O位具有不饱和取代基的2,3-脱氧-α-D-赤藓糖亨糖醛进行研究。用于1-O位取代基环化的底物是通过一种新型的氯化锌催化的Ferrier重排反应，将三-O-乙酰化的D-葡糖醛与不饱和醇反应而制备的，而用于4-O位取代基环化的底物则是通过烷基化或酰基化反应，对乙基6-O-保护的2,3-脱氧-α-D-赤藓糖亨糖醛进行处理。丙炔基取代基能有效环化，但丙烯基取代基则较差。丙炔酰基取代基在没有环化的情况下经历了氢锡化反应。

  DOI：

  10.1039/b000661k
• 作为产物：
  描述：

  D-葡萄糖 在 copper(ll) sulfate pentahydrate 、 氢溴酸 、 sodium acetate 、 四氯化碲 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.55h， 生成 but-3-yn-1-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions

  摘要：

  Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-D-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding a anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.073

文献信息

• Ceric(iv) ammonium nitrate-catalyzed glycosidation of glycals: a facile synthesis of 2,3-unsaturated glycosides
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Sushil Kumar Pandey

  DOI：10.1039/b009973m

  日期：——

  Glycosidation of glycals with alcohols in the presence of a catalytic amount of ceric(IV) ammonium nitrate under neutral conditions proceeds smoothly in refluxing acetonitrile to afford the corresponding 2,3-unsaturated glycosides in excellent yields.

  在温和条件下，以催化量的硝酸铈铵作为催化剂，糖酸内酯与醇在回流的乙腈中进行甘露糖基化反应，能够高效地生成相应的2,3-不饱和糖苷。
• 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
• Hafnium(IV) triflate as a highly efficient catalyst for Ferrier rearrangement of O- and S-nucleophiles with glycals
  作者：Yonghui Liu、Tianbang Song、Weijia Meng、Yun Xu、Peng George Wang、Wei Zhao

  DOI：10.1016/j.tetlet.2016.05.026

  日期：2016.6

  A highly efficient method to afford 2,3-unsaturated glycosides was described. In the presence of Hafnium(IV) triflate, a variety of 2,3-unsaturated-O- and S-glycosides have been obtained by stereoselective glycosylation of 3,4,6-tri-O-acetyl-d-glucal and hexa-O-acetyl-d-lactal with various acceptors in good isolated yields.

  描述了一种提供2，3-不饱和糖苷的高效方法。在铪（IV），三氟甲磺酸，各种2,3- unsaturated-存在ø -和š -glycosides已经通过的3,4,6-三-立体选择性糖基化得到ö乙酰基d -glucal和六ø乙酰基d -lactal在良好的分离产率的各种受体。
• 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。
• Copper(II) Triflate as a Mild and Efficient Catalyst for Ferrier Glycosylation: Synthesis of 2,3-Unsaturated O-Glycosides
  作者：Palakodety Radha Krishna、Sudhir Kashyap、Batthula Srinivas、Thurpu Reddy

  DOI：10.1055/s-0033-1341232

  日期：——

  Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)(2) as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.