tetra-O-acetyl-1,5-anhydro-L-glucitol | 912847-92-8

• 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: tetra-O-acetyl-1,5-anhydro-L-glucitol
• 英文别名: 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-galactitol；[(2S,3S,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 912847-92-8
• 化学式: C₁₄H₂₀O₉
• 分子量: 332.307
• InChiKey: ULWHEXUWXLOVPV-CRWXNKLISA-N

物化性质

• 保留指数：
  1886.52

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tetra-O-acetyl-1,5-anhydro-L-glucitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以95%的产率得到1,5-脱水-L-山梨糖醇
  参考文献：
  名称：

  Synthesis of aromatic C-xylosides by position inversion of glucose

  摘要：

  Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.068
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 偶氮二异丁腈 、 三正丁基氢锡 、 potassium fluoride 作用下， 以 乙醚 、 水 为溶剂， 反应 0.83h， 以0.844 g的产率得到tetra-O-acetyl-1,5-anhydro-L-glucitol
  参考文献：
  名称：

  Synthesis of aromatic C-xylosides by position inversion of glucose

  摘要：

  Two formally C-xylosylated analogs to 2-naphthyl beta-D-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position I becomes position 5). The D-C-xyloside showed priming, while the L-C-xyloside did not initiate priming. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.068

文献信息

• GLYCOSIDE COMPOUND AND PREPARATION METHOD THEREFOR, COMPOSITION, APPLICATION, AND INTERMEDIATE
  申请人：SHANGHAI HUTCHISON PHARMACEUTICALS LIMITED

  公开号：US20210115082A1

  公开（公告）日：2021-04-22

  The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.

  本发明公开了一种由III式表示的糖苷化合物，以及其制备方法、组合物、用途和中间体。本发明提供的糖苷化合物具有简单的制备方法，可以显著增加VEGF-A mRNA的表达，并且在促进血管生成方面具有有效性。这为开发具有促血管生成活性的药物治疗脑梗死、脑卒中、心肌梗死和下肢缺血微循环障碍提供了可靠的保证。
• Glycoside compound and preparation method therefor, composition, application, and intermediate
  申请人：SHANGHAI HUTCHISON PHARMACEUTICALS LIMITED

  公开号：US11325937B2

  公开（公告）日：2022-05-10

  The present invention discloses a glycoside compound represented by Formula III, and a preparation method, a composition, use and an intermediate thereof. The glycoside compound provided in the present invention has simple preparation method, can significantly increase the expression of VEGF-A mRNA, and is effective in promoting the angiogenesis. This provides a reliable guarantee for the development of drugs with pro-angiogenic activity for treating cerebral infarction cerebral stroke, myocardial infarction, and ischemic microcirculatory disturbance of lower limbs.

  本发明公开了一种由式 III 表示的糖苷化合物及其制备方法、组合物、用途和中间体。本发明提供的苷类化合物制备方法简单，能显著提高血管内皮生长因子-A mRNA的表达，有效促进血管生成。这为开发治疗脑梗塞脑中风、心肌梗塞、下肢缺血性微循环障碍等具有促血管生成活性的药物提供了可靠保证。