O²,O³,O⁴-Triacetyl-L-rhamnose | 130282-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O²,O³,O⁴-Triacetyl-L-rhamnose
• 英文别名: 2,3,4-Tri-o-acetyl-l-rhamnose；[(2R,3R,4S,5S)-3,4-diacetyloxy-5-hydroxy-1-oxohexan-2-yl] acetate
• CAS: 130282-67-6
• 化学式: C₁₂H₁₈O₈
• 分子量: 290.27
• InChiKey: MUKQRIORUXMVIO-CLVBZSDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O²,O³,O⁴-Triacetyl-L-rhamnose 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 (2R,3R,4R,5S,6S)-2-(((3RS,3aRS,7RS,9aRS,9bSR)-3a,6-dimethyl-5-oxo-3-(5-oxo-2,5-dihydrofuran-3-yl)-9b-((triethylsilyl)oxy)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-7-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Synthesis of BCD tricyclic analogues of the novel cardiac glycoside rhodexin A

  摘要：

  A concise synthesis of novel cardiac glycoside analogues of rhodexin A, 14 and 24, having the BCD tricyclic system is described. The key constructive step is an inverse-electron demand Diels-Alder reaction of the silyl enol ether 4 and the 2-acetyldiene, 7 and 15. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.114
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-甘露糖基溴化物 在 丙酮 、 silver carbonate 作用下， 生成 O²,O³,O⁴-Triacetyl-L-rhamnose
  参考文献：
  名称：

  Fischer et al., Chemische Berichte, 1920, vol. 53, p. 2362,2376, 2382

  摘要：

  DOI：

文献信息

• Glycosylated Warfarin Analogs and Uses Thereof
  申请人：Thorson Jon S.

  公开号：US20100267655A1

  公开（公告）日：2010-10-21

  The present invention discloses a set of glycosylated warfarin analogs which are useful as anti-tumor or anti-metastatic agents and as reagents for studying sugar uptake in cells.

  本发明公开了一组糖基化华法林类似物，可用作抗肿瘤或抗转移剂，并作为研究细胞糖吸收的试剂。
• GLYCOSYLATED CHLORAMBUCIL ANALOGS AND USES THEREOF
  申请人：Thorson Jon S.

  公开号：US20120094946A1

  公开（公告）日：2012-04-19

  A library of glycosylated chlorambucil analogs which are useful as anti-tumor and/or anti-metastatic agents is disclosed. The glycosylated chlorambucil analogs have the general formula wherein represents a reducing sugar moiety.

  揭示了一种作为抗肿瘤和/或抗转移药物有用的葡萄糖基氯氨丁醇类似物的图书馆。这些葡萄糖基氯氨丁醇类似物具有一般公式，其中表示还原糖基团。
• Ellipticine derivative and production process thereof
  申请人：SUNTORY LIMITED

  公开号：EP0173462A2

  公开（公告）日：1986-03-05

  An ellipticine derivative having the general formula: wherein R represents a hydrogen atom, a hydroxyl group, an alkoxyl group having 1 to 4 carbon atoms, or an acyloxy group having 2 to 7 carbon atoms; R2 represents an aldose residue, a deoxyaldose residue, an N-acylaminoaldose residue having a substituted acyl group with 2 to 4 carbon atoms bonded to the N atom, an aldohexuronic amide residue, and aldohexuronic acid residue, an acylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated N-acylaminoaldose residue having an amino group substituted with an acyl group with 2 to 4carbon atoms and having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an arylalkylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 7 to 8 carbon atoms, an arylalkylated N-acylaminoaldose residue having an amino group with an acyl group with 2 to 4 carbon atoms and having, substituted for the hydrogen of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms; and R3 represents a hydrogen atom, a linear, branched, cyclic, or cyclic-linear alkyl group having 1 to 5 carbon atoms; X0 represents a pharmaceutically acceptable inorganic or organic acid anion; and the bond represented by N⊕ - R2 in the general formula (I) represents a glycoside bond between a nitrogen atom in the 2-position of the ellipticine and a carbon atom in the 1-position of the sugar. These ellipticine derivatives have a strong antineoplastic or antitumor activity and, therefore, are expected to be effective as an antineoplastic or antitumor agent.

  一种具有通式的鞣花碱衍生物： 其中 R 代表氢原子、羟基、具有 1 至 4 个碳原子的烷氧基或具有 2 至 7 个碳原子的酰氧基； R2 代表醛糖残基、脱氧醛糖残基、N-酰氨基醛糖残基（其 N 原子上键有 2 至 4 个碳原子的取代酰基）、醛缩脲酰胺残基、醛缩脲酸残基、酰化醛糖残基（其糖羟基的氢原子被取代）、一种酰化脱醛糖残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化的 N-酰氨基醛糖残基，其氨基被 2 至 4 个碳原子的酰基取代，并具有 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代糖羟基的氢原子；酰化的醛缩酰胺残基，其具有一种酰化的醛缩己脲酰胺残基，其糖的羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化醛缩醛酸酯残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷基酰基或 7 至 9 个碳原子的芳基酰基取代、芳烷基化脱醛糖残基，其糖的羟基的氢原子被 7 至 8 个碳原子的烷酰基取代；芳烷基化 N-酰氨基醛糖残基，其氨基带有 2 至 4 个碳原子的酰基，并具有一种芳烷基化的醛缩脲酰胺残基，其氨基具有 2 至 4 个碳原子的酰基，并具有 7 至 8 个碳原子的芳烷基取代糖的羟基的氢原子、一种芳烷基化的醛缩脲酸酯残基，其糖的羟基的氢原子被具有 7 至 8 个碳原子的芳烷基取代；和 R3 代表氢原子、具有 1 至 5 个碳原子的直链、支链、环状或环状直链烷基； X0 代表药学上可接受的无机或有机酸阴离子；以及 通式（I）中 N⊕ - R2 所代表的键代表鞣花碱 2 位上的氮原子与糖 1 位上的碳原子之间的糖苷键。这些鞣花碱衍生物具有很强的抗肿瘤或抗肿瘤活性，因此有望成为有效的抗肿瘤或抗肿瘤药物。
• US4698423A
  申请人：——

  公开号：US4698423A

  公开（公告）日：1987-10-06
• US8278436B2
  申请人：——

  公开号：US8278436B2

  公开（公告）日：2012-10-02