3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose | 56824-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose
• 英文别名: (1R,2S,5R,7R)-spiro[3,6,8,10-tetraoxatricyclo[5.3.0.02,5]decane-9,1'-cyclohexane]
• CAS: 56824-28-3
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: WUVNAZOLJMBYDH-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose 在 甲基碘化镁 、 硫酸 、 sodium 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 17.5h， 生成 methyl 5-O-benzyl-α-D-xylofuranoside
  参考文献：
  名称：

  格氏试剂在碳水化合物合成中的应用。三、甲基呋喃糖苷的单向异构化及其呋喃糖环的开环

  摘要：

  甲基呋喃糖苷衍生物与甲基碘化镁或叔丁基溴化镁的异构化以单向方式发生。例如，当 3β 和叔丁基溴化镁在苯-醚中的混合物加热时，甲基 5-O-苄基-β-D-呋喃核糖苷 (3β) 以 95% 的产率转化为相应的 α-异头物 (3α)在约 75°C 下除去乙醚；逆反应（从3α到（3β）没有进行。3β与甲基碘化镁反应得到开链产物（33%），除3α（30%）外，还测试了20种异头异构体，并对其作用机理进行了研究。在反应过程中也观察到用格氏试剂裂解苄基或三苯甲基保护基团。

  DOI：

  10.1246/bcsj.54.1492
• 作为产物：
  描述：

  1,2-O-Cyclohexylidene-α-D-xylofuranose 在 吡啶 、 碘 、 三苯基膦 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以60%的产率得到3,5-anhydro-1,2-O-cyclohexylidene-α-D-xylofuranose
  参考文献：
  名称：

  通过phospho离子诱导的碘化和碱催化的威廉姆森醚化反应，使一元醇从二醇中简单地一锅式进入到各种环大小的环醚中

  摘要：

  已经建立了使用三苯基膦，碘和含氮碱的新颖且有效的一锅环化方法，用于合成各种环大小的环醚。这似乎遵循两步程序，其中包括一个羟基被原位生成的碘优先取代，然后通过游离羟基或更多亲核性氧化物离子的攻击而分子内闭环。

  DOI：

  10.1016/j.tetlet.2006.08.090

文献信息

• Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone
  作者：Velimir Popsavin、Bojana Srećo、Goran Benedeković、Jovana Francuz、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.ejmech.2010.03.010

  日期：2010.7

  This paper describes a straightforward divergent synthesis of (+)-goniofufurone mimics (4, 5 and 6) starting from d-xylose. In a preliminary bioassay, analogues 4 and 5 exhibited a submicromolar antiproliferative activity towards HL-60 cells, while the corresponding parent compound 1 was completely inactive against this cell line. At the same time, these molecules showed approximately 10-fold stronger

  本文描述的（+）一个简单的发散合成- goniofufurone模拟物（4，5和6）从起始d木糖。在初步的生物测定中，类似物4和5对HL-60细胞表现出亚微摩尔的抗增殖活性，而相应的母体化合物1对该细胞系完全没有活性。同时，与标准抗癌药阿霉素（DOX）相比，这些分子在同一细胞系中显示出约10倍更强的细胞毒性。与对照化合物1相比，类似物6在Raji细胞系中显示出18倍和3倍的效力和DOX分别。还公开了从d-木糖制备（+）-gonfufufurone（1）和（+）-crassalactone C（3）的新的分歧路线。
• Alkylating ability of carbohydrate oxetanes: Practical synthesis of bolaform skeleton derivative
  作者：Pavle Hadzic、Mirjana Popsavin、Suncica Borozan

  DOI：10.2298/jsc150224033h

  日期：——

  Alkylating ability of oxetane ring in carbohydrate structure was investigated and flexible method for bolaform amphiplile skeleton construction with xylose as polar heads is proposed. The method is based on oxetane ring opening in easily accessible 3,5-anhydro-1,2-O-cyclohexylidenexylofuranose (1). One step nitrogen alkylation in terminal diamines with 1 gave basic cationic bolaform skeleton with xylose as potential polar heads and deliberately chosen length of non polar spacer. Under similar experimental conditions, but with appropriate molar ratio of alkylating agent, alkylation reaction provide for selective monoalkylation of diamines. Successful alkylation in xanthine series (theophylline) was also achieved with 1, giving a new 5-deoxy-5-(7?-theophyllineamino)-?-D-xylofuranose derivative.

  研究了碳水化合物结构中氧杂环的烷化能力 的烷化能力，并提出了以木糖为极性头构建双链烯骨架的灵活方法。 提出了以木糖为极性头构建双链烯骨架的灵活方法。该方法基于氧杂环 开环为基础。 (1).在 1 的末端二胺中进行一步氮烷基化，就能得到基本的 以木糖为潜在极性头和特意选择的非极性间隔长度的阳离子双核骨架。 特意选择的非极性间隔长度。在类似的实验条件下 在类似的实验条件下，但使用适当摩尔比的烷基化剂，烷基化反应可提供选择性的单烷氧基化。 反应可对二胺进行选择性单烷基化。成功的 在黄嘌呤系列（茶碱）中，用 1、 得到了一种新的 5-脱氧-5-（7-茶碱氨基）-D-氧基呋喃糖衍生物。
• Heteroannelated (+)-muricatacin mimics: synthesis, antiproliferative properties and structure–activity relationships
  作者：Bojana Srećo、Goran Benedeković、Mirjana Popsavin、Pavle Hadžić、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković、Velimir Popsavin

  DOI：10.1016/j.tet.2011.09.132

  日期：2011.12

  Six new (+)-muricatacin mimics bearing a furano-furanone core have been synthesized and their in vitro antiproliferative activity was evaluated against a panel of human tumour cell lines. A straightforward total synthesis of (+)-muricatacin (1) from D-xylose is disclosed providing a sample of 1 that served as a positive control in antitumour assays. All new compounds showed diverse antiproliferative effects against human malignant cell lines, but were devoid of any significant cytotoxicity towards the normal foetal lung fibroblasts (MRC-5). Additionally, the most of (+)-muricatacin analogues show selective cytotoxicities towards certain cancer cell lines, whereas only two of six analogues are broadly toxic against all cell lines under evaluation. A SAR study reveals the structural features that may be beneficial for the antiproliferative activity of these lactones. These include the absolute stereochemistry, introduction of a THF ring, interchange of the O-8 ether functionality and the C-8 methylene group in the side chain of muricatacin oxa analogues, as well as the one- or two-carbon homologation of the side chain in both 3 and 6. (C) 2011 Elsevier Ltd. All rights reserved.
• Efficient nitrogen alkylation with carbohydrates
  作者：Pavle Hadžić、Nada Vukojević

  DOI：10.1016/s0008-6215(03)00114-9

  日期：2003.5

  Efficient nitrogen alkylation of various primary and secondary amines, including cyclic, heterocyclic and alkaloid type amines, with a sugar oxetane 3,5-anhydro-1,2-O-cyclohexylidene-alpha-D-xylofuranose is described. As a result, 5-amino-5-deoxy derivatives of xylofuranose were obtained in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• From d-xylose to terminal polyols: a simple synthetic route
  作者：Pavle Hadzic、Mirjana Popsavin

  DOI：10.1016/j.carres.2009.12.006

  日期：2010.2

  A simple and efficient synthetic approach toward different terminal alkyl tetraols and triols, starting from D-xylose, is described. The opening of the oxetane ring in a suitably protected 3,5-anhydro-D-xylose derivative with Grignard reagents leads to D-Xylose-derived 5-deoxy-5-C-alkyl derivatives, which are suitable for reduction to terminal polyols after protecting group hydrolysis. (C) 2009 Elsevier Ltd. All rights reserved.