allyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside | 135824-47-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: allyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: allyl 2-deoxy-3,4,6-tri-O-acetyl-D-galactopyranoside；allyl 3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranoside；[(2R,3R,4R,6R)-3,4-diacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 135824-47-4
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: FFCOCBVSYDMDEH-KBUPBQIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三甲基溴硅烷 、 氢溴酸 、 溶剂黄146 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 allyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranoside 、 allyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  摘要：

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。

  DOI：

  10.3762/bjoc.12.164

文献信息

• Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
  作者：Ornelio Rosati、Massimo Curini、Federica Messina、Maria Carla Marcotullio、Giancarlo Cravotto

  DOI：10.1007/s10562-012-0932-z

  日期：2013.2

  conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.Graphical Abstract

  层状 α-磺基苯基膦酸锆 - 甲膦酸是一种固体酸催化剂，可在温和的反应条件下，在短时间内和良好的产率催化 d-乙二醇和醇类亲核试剂的费里尔重排。值得注意的是，α-磺基苯基膦酸锆-甲膦酸锆和溴化锂的组合改变了该过程的区域选择性，以良好的收率提供了 2-脱氧糖。
• Ring-rearrangement metathesis of substituted dihydropyrans and dihydrofurans
  作者：Morgan Donnard、Théophile Tschamber、Didier Le Nouën、Sandy Desrat、Karen Hinsinger、Jacques Eustache

  DOI：10.1016/j.tet.2010.11.036

  日期：2011.1

  The rearrangement of dihydropyrans and dihydrofurans featuring appending olefins has been studied. The rearranged products bear resemblance with polyunsaturated di- and trisaccharides. Examples of functionalization prior to, or following, rearrangement are provided suggesting that the method should be useful for the synthesis of nonclassical saccharides. This work also illustrates the power of cascade

  已经研究了以附加烯烃为特征的二氢吡喃和二氢呋喃的重排。重排产物与多不饱和二糖和三糖相似。提供了在重排之前或之后的官能化的实例，表明该方法应可用于合成非经典糖类。这项工作还说明了级联介观过程从相对简单的杂环开始增加分子复杂性的能力。
• α-Selective synthesis of 2-deoxy-glycosides and disaccharides
  作者：Guofang Yang、Xiaosheng Luo、Hong Guo、Qingbing Wang、Jiafen Zhou、Tianyun Huang、Jie Tang、Junjie Shan、Jianbo Zhang

  DOI：10.1080/07328303.2018.1439498

  日期：2018.3.24

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.
• Synthesis of 2-deoxy sugars from glycals
  作者：Subramaniam Sabesan、Susana Neira

  DOI：10.1021/jo00018a054

  日期：1991.8
• US5128463A
  申请人：——

  公开号：US5128463A

  公开（公告）日：1992-07-07