tri-O-benzoyl-ξ-D-xylopyranosyl bromide | 145374-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tri-O-benzoyl-ξ-D-xylopyranosyl bromide
• 英文别名: [(3R,4S,5R)-4,5-dibenzoyloxy-6-bromooxan-3-yl] benzoate
• CAS: 145374-03-4
• 化学式: C₂₆H₂₁BrO₇
• 分子量: 525.353
• InChiKey: WZNBMSMEBBTFBW-VNYJYPEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tri-O-benzoyl-ξ-D-xylopyranosyl bromide 在 吡啶 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  THIOPYRANOSE COMPOUND AND METHOD FOR PRODUCING SAME

  摘要：

  提供了一种通过将以下式（1）代表的化合物与硫化合物反应来制备由以下式（2）表示的硫代吡喃糖化合物的生产方法。X代表一个离去基团。A代表一个氧原子或硫原子。此外，R1A到R4B，R1B到R4B和R5分别代表氢原子或特定取代基。

  公开号：

  US20160355497A1
• 作为产物：
  描述：

  tetrabenzoyl-D-xylopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以4.85 g的产率得到tri-O-benzoyl-ξ-D-xylopyranosyl bromide
  参考文献：
  名称：

  THIOPYRANOSE COMPOUND AND METHOD FOR PRODUCING SAME

  摘要：

  提供了一种通过将以下式（1）代表的化合物与硫化合物反应来制备由以下式（2）表示的硫代吡喃糖化合物的生产方法。X代表一个离去基团。A代表一个氧原子或硫原子。此外，R1A到R4B，R1B到R4B和R5分别代表氢原子或特定取代基。

  公开号：

  US20160355497A1

文献信息

• Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
  作者：Ying-Hsin Wang、Hsien-Wei Yeh、Hsiao-Wen Wang、Chia-Chun Yu、Jih-Hwa Guh、Der-Zen Liu、Pi-Hui Liang

  DOI：10.1016/j.carres.2013.04.022

  日期：2013.6

  Naturally occurring spirostanol saponins bear a chacotriose, alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyr anose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2' and/or 4' positions of chacotriose is

  天然存在的螺固醇皂苷带有低聚部分的三甘醇，α-L-鼠李糖基-（1-> 2）-[α-L-鼠李糖基-（1-> 4）]-β-D-葡萄糖吡喃糖残基。据信对于生物学活性是重要的。在本文中，描述了一种简明的组合方法的开发，该方法用于合成在chacotriose的2'和/或4'位置上的两个系列的聚糖变体，并研究了叶绿素在3-OH处的糖苷部分的结构-活性关系。发现这些化合物对白血病细胞系CCRF和HL-20的细胞毒性较弱，表明茶三糖部分对于抗癌活性很重要。
• Synthesis of compounds related to antitumor agents. II. Studies on the synthesis of oxazolo(4,5-d)pyrimidine nucleoside derivatives.
  作者：ISOO ITO、NORIICHI ODA、TETSUO KATO、KAZUO OTA

  DOI：10.1248/cpb.23.2104

  日期：——

  2, 4-Diamino-6-methylpyrimidine (II) was synthesized from acetoacetonitrile (III) and guanidine which was then converted to 5-amino-7-methyloxazolo [4, 5-d] pyrimidin-2(3H)-one(IX). Several nucleoside type compounds were synthesized by the condensation of IX with some halogenoacetyl and halogenobenzoyl sugars in the presence of metal salts as a halogen acceptor. The antitumor activity of the compounds was tested and found to be inactive.

  由乙酰乙腈(III)和胍合成2, 4-二氨基-6-甲基嘧啶(II)，然后将其转化为5-氨基-7-甲基恶唑并[4, 5-d]嘧啶-2(3H)-酮(IX ）。在金属盐作为卤素受体的存在下，通过 IX 与一些卤代乙酰基和卤代苯甲酰糖的缩合合成了几种核苷型化合物。测试了这些化合物的抗肿瘤活性，发现没有活性。
• A Cu(OTf)₂-Catalyzed Glycosylation with Glycosyl <i>ortho</i>-<i>N</i>-Phthalimidoylpropynyl Benzoates as Donors
  作者：Bei-Bei Zhan、Kai-Sheng Xie、Qian Zhu、Weiping Zhou、Dapeng Zhu、Biao Yu

  DOI：10.1021/acs.orglett.3c01163

  日期：2023.6.2

  A Cu(OTf)2-catalyzed glycosylation protocol using glycosyl ortho-N-phthalimidoylpropynyl benzoates (NPPBs) as donors was disclosed, which features an inexpensive copper catalyst, operationally convenient conditions, high to excellent yields, and a broad substrate scope. Mechanistic studies indicated an isochromen-4-yl copper(II) intermediate arising from the departure of the leaving group.

  公开了一种使用糖基邻-N-邻苯二甲酰亚胺基丙炔基苯甲酸酯 (NPPB) 作为供体的Cu(OTf) 2催化糖基化方案，该方案具有廉价的铜催化剂、操作方便的条件、高至优异的产率和广泛的底物范围。机理研究表明离去基团的离去产生了 isochrome-4-yl copper(II) 中间体。
• 10.1016/j.bmc.2024.117737
  作者：Sylla, Balla、Jost, Gilles、Lavoie, Serge、Legault, Jean、Gauthier, Charles、Pichette, André

  DOI：10.1016/j.bmc.2024.117737

  日期：——

  of ursane-type pentacyclic triterpenoids for pharmacological use is their poor aqueous solubility, which can impede their effectiveness as therapeutics agents. In this study, we present the facile synthesis of ursolic acid monodesmosides and uvaol bidesmosides, incorporating naturally occurring and water-soluble pentoses and deoxyhexose sugar moieties of opposite and -configurations at the C3 or C3/C28

  熊果酸和山楂醇是天然存在的三萜类化合物，具有广泛的药理活性，包括细胞毒性。然而，开发用于药理学用途的乌苏烷型五环三萜类化合物的主要挑战是它们的水溶性差，这可能妨碍它们作为治疗剂的有效性。在这项研究中，我们提出了熊果酸单链苷和乌苏醇双链苷的简便合成，在乌苏烷核心的C3或C3/C28位置掺入了天然存在的水溶性戊糖和脱氧己糖部分的相反和-构型。评估了二十种合成皂苷对肺癌（A549）和结直肠腺癌（DLD-1）细胞系的细胞毒性。值得注意的是，与它们的非细胞毒性母体三萜类化合物相比，所有双锁链乌苏醇皂苷均显示出细胞毒性。对于每个乌苏烷型皂苷系列，最活跃的化合物是 3--α 阿拉伯吡喃糖基熊果酸 () 和 3,28-二-α 吡喃鼠李糖基乌索醇 ()，显示出针对 A549 和 DLD-1 癌症的低微摩尔范围内的 IC 值线。
• Discovery of 4-functionalized phenyl-O-β-d-glycosides as a new class of mushroom tyrosinase inhibitors
  作者：Wei Yi、Rihui Cao、Huan Wen、Qin Yan、Binhua Zhou、Lin Ma、Huacan Song

  DOI：10.1016/j.bmcl.2009.09.018

  日期：2009.11

  A series of 4-functionalized phenyl-O-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that compounds 6a-13a bearing a thiosemicarbazide moiety exhibited potent activities with IC50 values range from 0.31 to 52.8 mu M. Particularly, compound 9a containing acetylated glucose moiety was found to be the most active molecule with an IC50 value of 0.31 mu M. SARs analysis suggested that (1) the thiosemicarbazide moiety remarkably contributed to the increase of inhibitory effects on tyrosinase; (2) the configuration and bond type of sugar moiety also played a very important role in determining their inhibitory activities. The inhibition kinetics and inhibition mechanism study revealed that compound 9a was reversible and competitive type inhibitor, whereas compound 13a was reversible and competitive-uncompetitive mixed-II type inhibitor. (c) 2009 Published by Elsevier Ltd.