methyl 2-O-(2-methylpropanoyl)-3,4-O-isopropylidene-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 2-O-(2-methylpropanoyl)-3,4-O-isopropylidene-β-D-galactopyranoside
• 英文别名: methyl 2-O-isobutyryl-3, 4-O-isopropylidene-beta-D-galactopyranoside；methyl 2-O-isobutyryl-3,4-O-isopropylidene-beta-D-galactopyranoside；[(3aS,4R,6R,7R,7aS)-4-(hydroxymethyl)-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] 2-methylpropanoate
• 化学式: C₁₄H₂₄O₇
• 分子量: 304.34
• InChiKey: PNDFXNZZGLXKBV-VFZGUZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside 在 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 0.5h， 生成 methyl 2-O-(2-methylpropanoyl)-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation and evaluation of the in vitro erythroid differentiation induction properties of some esters of methyl 3,4-O-isopropylidene-β-d-galactopyranoside and 2,3-O-isopropylidene-d-mannofuranose

  摘要：

  Two series of glycide esters of short fatty acids, designed for avoiding intramolecular transesterification, were prepared and tested for in vitro erythroid differentiation induction activities using the K562 cell line as experimental system. The 6-O-isobutiryl and pivaloyl derivatives of methyl 3,4-O-isopropylidene-beta -D-galactopyranosides as well the same 1-O-esters of 2,3-O-isopropylidene-alpha- and beta -D-mannofuranose nose exhibit biological activities much higher that the corresponding acids and could be proposed as possible agents to modulate production of embryo-fetal hemoglobins by human erythroid cells. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00285-1

文献信息

• Glucidic esters of branched carboxylic acids capable of inducing erythroid cellular differentiation
  申请人：ASSOCIAZIONE VENETA PER LA LOTTA ALLA TALASSEMIA

  公开号：EP1004590A2

  公开（公告）日：2000-05-31

  The present invention provides compounds which are esters of a carbohydrate, constituted by a carbohydrate unit or a glycoside derived therefrom, having at least one alcohol group esterified with a branched chain carboxylic acid and having the remaining alcohol groups in part protected with a protector group, such as an isopropylidene group, and partly in the form of free hydroxyls. These carbohydrate esters being provided with a significant biological activity as erythroid cellular differentiation inducers can be utilised for the preparation of a medicament for the therapeutic treatment of β-talaxemia or tumours.

  本发明提供的化合物是一种碳水化合物的酯类，由碳水化合物单元或由其衍生的糖苷构成，具有至少一个醇基与支链羧酸酯化，并且其余的醇基部分被保护为保护基团，例如异丙基亚甲基基团，部分以自由羟基的形式存在。这些碳水化合物酯类具有显著的生物活性，可以诱导红细胞分化，可用于制备治疗β-地中海贫血或肿瘤的药物。
• Preparation and evaluation of the in vitro erythroid differentiation induction properties of some esters of methyl 3,4-O-isopropylidene-β-d-galactopyranoside and 2,3-O-isopropylidene-d-mannofuranose
  作者：Giorgio Catelani、Felicia D'Andrea、Ettore Mastrorilli、Nicoletta Bianchi、Cristiano Chiarabelli、Monica Borgatti、Dino Martello、Roberto Gambari

  DOI：10.1016/s0968-0896(01)00285-1

  日期：2002.2

  Two series of glycide esters of short fatty acids, designed for avoiding intramolecular transesterification, were prepared and tested for in vitro erythroid differentiation induction activities using the K562 cell line as experimental system. The 6-O-isobutiryl and pivaloyl derivatives of methyl 3,4-O-isopropylidene-beta -D-galactopyranosides as well the same 1-O-esters of 2,3-O-isopropylidene-alpha- and beta -D-mannofuranose nose exhibit biological activities much higher that the corresponding acids and could be proposed as possible agents to modulate production of embryo-fetal hemoglobins by human erythroid cells. (C) 2001 Elsevier Science Ltd. All rights reserved.