methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside | 20880-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside
• 英文别名: methyl α-D-xylopyranoside triacetate；Methyl-(2,3,4-tri-O-acetyl-α-D-xylopyranosid)；(3R,4S,5R,6S)-4,5-bis(acetyloxy)-6-methoxyoxan-3-yl acetate；[(3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxyoxan-3-yl] acetate
• CAS: 20880-54-0
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: YBESHGJFPWHRBW-KXNHARMFSA-N

物化性质

• 熔点：
  86 °C
• 沸点：
  332.1±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside 在 氢氟酸 作用下， 反应 2.0h， 生成 2,3,4-tri-O-acetyl-α-D-xylopyranosyl fluoride
  参考文献：
  名称：

  A one-pot procedure for the quantitative conversion of glycosides into acetylated glycosyl fluorides

  摘要：

  DOI：

  10.1016/0008-6215(95)00328-2
• 作为产物：
  描述：

  甲基2,3,4-三-O-乙酰基-beta-D-吡喃木糖 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside
  参考文献：
  名称：

  氯化铁，一种用于制备烷基α-吡喃葡萄糖苷的阴离子化催化剂

  摘要：

  已经发现CH 2 Cl 2中的无水FeCl 3可以在室温下以良好的产率和选择性将β-糖吡喃糖苷容易地异构化为其相应的α-端基异构体。乙酰基和苯甲酰基保护的氧糖产生了最好的结果。

  DOI：

  10.1016/s0040-4039(00)74242-0

文献信息

• Methanolysis of acetylated sugars and glycosides in the presence of tin oxides and alkoxides
  作者：Jacob Herzig、Abraham Nudelman、Hugo E. Gottlieb

  DOI：10.1016/0008-6215(88)85038-9

  日期：1988.6

  Abstract A simple, regioselective O -deacetylation procedure is described which involves ⩽0.5 equiv. of Bu 3 SnOMe or Bu 2 SnO in methanol. Anomeric acetates are considerably more reactive than primary and secondary acetates, thereby enabling selective removal, to give ∼70% of products with HO-1 unsubstituted. Prolonged reaction resulted in complete deacetylation. Secondary acetates were removed faster

  摘要描述了一种简单的区域选择性O-脱乙酰化方法，涉及involves0.5当量。甲醇中的Bu 3 SnOMe或Bu 2 SnO的混合物。端粒的乙酸盐比起伯乙酸盐和仲乙酸盐具有更高的反应活性，因此能够选择性地除去，从而得到约70％的HO-1未取代的产物。长时间的反应导致完全脱乙酰。仲乙酸盐的去除速度比伯乙酸盐更快，并且反应的总速率受OAc OH⪢OMe顺序的异头取代基影响很大。在反应条件下没有酰基迁移发生。
• Selective deuteration over raney nickel in deuterium oxide: Methyl glycosides
  作者：Stephen J. Angyal、John D. Stevens、Léon Odier

  DOI：10.1016/0008-6215(86)85061-3

  日期：1986.12

  by deuterated Raney nickel in deuterium oxide, in various positions in methyl glycopyranosides and furanosides has been studied. In general, the exchange process is not highly regio-selective in these compounds. However, conditions were found under which methyl β- d -fructopyranoside can be selectively labelled on C-5, methyl β- d -fructofuranoside on C-3, and methyl β- d -galactopyranoside on C-3

  摘要研究了氘代阮内镍在氧化氘中甲基吡喃葡萄糖苷和呋喃糖苷中不同位置催化的-氘交换速率。通常，在这些化合物中，交换过程不是高度区域选择性的。然而，发现了可以在C-5上选择性标记甲基β-d-果糖吡喃糖苷，在C-3上选择性标记甲基β-d-果糖呋喃糖苷以及在C-3和C-4上标记甲基β-d-半乳糖吡喃糖苷的条件。
• Structure and Synthesis of Miyaginin, a<i>p</i>-Allylphenyl Glycoside from<i>Lespedeza thunbergii</i>forma<i>macrantha</i>
  作者：Makoto Ojika、Hiroki Kuyama、Haruki Niwa、Kiyoyuki Yamada

  DOI：10.1246/bcsj.57.2893

  日期：1984.10

  The structure of miyaginin previously reported as p-vinylphenyl O-d-xylosyl-(1→6)-d-glucoside without stereochemical assignment of two glycosidic linkages was reinvestigated by spectral and chemical means and shown to be revised as p-allylphenyl O-β-d-xylopyranosyl-(1→6)-β-d-glucopyranoside (p-allylphenyl β-primeveroside). In order to confirm the revised structure, an unambiguous synthesis of miyaginin was performed.

  早前报道的miyaginin结构为对乙烯基苯基 O-β-木糖基-(1→6)-β-葡萄糖苷，但未指明两个糖苷键的立体化学配置。通过光谱和化学方法重新研究后，发现其结构应修正为对丙烯基苯基 O-β-d-木吡喃糖基-(1→6)-β-d-葡吡喃糖苷（对丙烯基苯基 β-衍生物）。为了确认修正后的结构，进行了明确的miyaginin合成。
• ISOLATION AND STRUCTURES OF TWO NEW<i>p</i>-HYDROXYSTYRENE GLYCOSIDES, PTELATOSIDE-A AND PTELATOSIDE-B FROM BRACKEN,<i>PTERIDIUM AQUILINUM</i>VAR.<i>LATIUSCULUM</i>, AND SYNTHESIS OF PTELATOSIDE-A
  作者：Makoto Ojika、Kazumasa Wakamatsu、Haruki Niwa、Kiyoyuki Yamada、Iwao Hirono

  DOI：10.1246/cl.1984.397

  日期：1984.3.5

  Two new p-hydroxystyrene glycosides, ptelatoside-A and ptelatoside-B were isolated from the carcinogenic fraction of aqueous extracts of bracken, Pteridium aquilinum var. latiusculum, and their structures were established to be p-β-primeverosyloxystyrene and p-β-neohesperidosyloxystyrene, respectively by chemical and spectral means. A synthesis of ptelatoside-A was achieved.

  从蕨类植物 Pteridium aquilinum var. latiusculum 的水提取物致癌部分中分离出了两种新的对羟基苯乙烯苷-ptelatoside-A 和 ptelatoside-B，并通过化学和光谱手段确定了它们的结构分别为 p-β-primeverosyloxystyrene 和 p-β-neohesperidosyloxystyrene。实现了葇荑苷-A 的合成。
• Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US10953027B2

  公开（公告）日：2021-03-23

  Disclosed herein are active agents, compositions containing them, unit dosage forms containing them, and methods of their use, e.g., for treating a metabolic disorder or nonalcoholic fatty liver disease or for modulating a metabolic marker or nonalcoholic fatty liver disease marker.

  本文公开了活性剂、含有活性剂的组合物、含有活性剂的单位剂型以及活性剂的使用方法，例如用于治疗代谢紊乱或非酒精性脂肪肝或调节代谢标志物或非酒精性脂肪肝标志物。