1-O-butanoyl-β-D-glucopyranose | 86784-51-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-butanoyl-β-D-glucopyranose
• 英文别名: 1-O-butyroyl-β-D-glucopyranose；beta-3-glucosyl butyrate；glucose butyrate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] butanoate
• CAS: 86784-51-2
• 化学式: C₁₀H₁₈O₇
• 分子量: 250.249
• InChiKey: MTLDSTPGZPRTSK-HOQQJHGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,6-anhydro-β-L-idopyranose 在 CH₃OH,Amberlite-IRA-400(HCO₃^-) 、 sodium 2,2,2-trifluoroacetate 、 溴化钛(IV) 作用下， 以 苯 为溶剂， 反应 101.08h， 生成 1-O-butanoyl-β-D-glucopyranose
  参考文献：
  名称：

  一种新的合成方法，使用三邻三氟乙酰基-1,6-脱水葡萄糖合成1-O-酰基-8-吡喃葡萄糖。Tuliposide-A的合成。

  摘要：

  三-O-三氟乙酰基-1,6-脱水葡萄糖被证明是1β-O-酰基葡萄糖的有用前体。在沸腾的CF 3 COOH中用TiBr 4处理得到2,3,4,6-四-O-三氟乙酰基-α-D-吡喃葡萄糖基溴化物，其与苯中的羧酸银反应生成1β-O-酰基衍生物。通过使化合物与甲醇接触或通过氧化铝色谱法除去TFA基团，得到1β-O-酰基-D-吡喃葡萄糖。通过该方法，合成了Tuliposide-A，1-O-（γ-羟基-α-亚甲基丁酰基）-β-D-吡喃葡萄糖。

  DOI：

  10.1016/s0040-4039(00)88020-x

文献信息

• GLUCOPYRANOSYLOXYBENZYLBENZENE DERIVATIVES AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1329456A1

  公开（公告）日：2003-07-23

  The present invention relates to glucopyranosyloxybenzylbenzene derivatives represented by the general formula: wherein P represents a group forming a prodrug; and R represents a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkoxy-substituted (lower alkyl) group, a lower alkoxy-substituted (lower alkoxy) group or a lower alkoxy-substituted (lower alkylthio) group, which have an improved oral absorption and can exert an excellent inhibitory activity in human SGLT2 in vivo and which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, and pharmaceutical compositions comprising the same.

  本发明涉及由通式表示的葡糖基吡喃氧基苄基苯衍生物： 其中 P 代表形成原药的基团；R代表低级烷基、低级烷氧基、低级烷硫基、低级烷氧基取代的（低级烷基）基团、低级烷氧基取代的（低级烷氧基）基团或低级烷氧基取代的（低级烷硫基）基团、它们具有更好的口服吸收性，并能在体内对人类 SGLT2 发挥出色的抑制活性，可用作预防或治疗与高血糖有关的疾病（如糖尿病、糖尿病并发症或肥胖症）的制剂，以及包含这些制剂的药物组合物。
• NOVEL AROMATIC ACYL GROUP TRANSFERASE GENE
  申请人：Aomori prefecture

  公开号：EP1947179A1

  公开（公告）日：2008-07-23

  The present invention provides a protein having the amino acid sequence as shown in SEQ ID NO: 2, 4, 6, 8, 10 or 12 or a protein having a modified amino acid sequence thereof and having an activity of transferring an aromatic acyl group to a sugar residue of a flavonoid; a gene, especially cDNA, encoding the protein; and use thereof For example, by introducing the above gene into a plant expressing hydroxycinnamate 1-O-glucosyltransferase gene, optionally together with a cDNA encoding a protein having the amino acid sequence as shown in SEQ ID NO: 14, 16 or 18 or a protein having an amino acid sequence derived therefrom by modification and having an activity of glucosylating a hydroxyl group at position 1 of hydroxycinnamic acid, and then expressing the introduced gene(s), it is possible to acylate the sugar residue of flavonoids in flowers of the plant to thereby confer a blue color on the flowers.

  本发明提供了一种具有 SEQ ID NO：2、4、6、8、10 或 12 所示氨基酸序列的蛋白质，或其氨基酸序列经修饰并具有将芳香酰基转移到类黄酮的糖残基上的活性的蛋白质；编码该蛋白质的基因，特别是 cDNA；及其用途 例如，将上述基因导入表达羟基肉桂酸 1-O-葡萄糖基转移酶基因的植物中，任选与编码具有 SEQ ID NO：14、16 或 18 所示氨基酸序列的蛋白质，或其氨基酸序列经修饰后得到的具有羟基肉桂酸 1 位羟基葡萄糖基化活性的蛋白质，然后表达导入的基因，就可以使植物花朵中黄酮类化合物的糖残基酰化，从而使花朵呈现蓝色。
• Bols, Mikael; Hansen, Henrik Claus, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 818 - 822
  作者：Bols, Mikael、Hansen, Henrik Claus

  DOI：——

  日期：——
• NOVEL AROMATIC ACYL GROUP TRANSFERASE GENES
  申请人：Local Independent Administrative Institution Aomori Prefectural Industrial Technology Research Center

  公开号：EP1947179B1

  公开（公告）日：2011-09-21
• Novel Aromatic Acyltransferase Genes
  申请人：Noda Naonobu

  公开号：US20090288225A1

  公开（公告）日：2009-11-19

  The present invention provides a protein having the amino acid sequence as shown in SEQ ID NO: 2, 4, 6, 8, 10 or 12 or a protein having a modified amino acid sequence thereof and having an activity of transferring an aromatic acyl group to a sugar residue of a flavonoid; a gene, especially cDNA, encoding the protein; and use thereof. For example, by introducing the above gene into a plant expressing hydroxycinnamate 1-O-glucosyltransferase gene, optionally together with a cDNA encoding a protein having the amino acid sequence as shown in SEQ ID NO: 14, 16 or 18 or a protein having an amino acid sequence derived therefrom by modification and having an activity of glucosylating a hydroxyl group at position 1 of hydroxycinnamic acid, and then expressing the introduced gene(s), it is possible to acylate the sugar residue of flavonoids in flowers of the plant to thereby confer a blue color on the flowers.