[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[3-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-en-2-ylsulfinyl]phenyl]sulfinylprop-2-enoxy]oxan-2-yl]methyl acetate | 1139695-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[3-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-en-2-ylsulfinyl]phenyl]sulfinylprop-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 1139695-49-0
• 化学式: C₄₀H₅₀O₂₂S₂
• 分子量: 946.956
• InChiKey: WHIRWCCPWXAVOU-CESRUUPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  64
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  320
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[3-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-en-2-ylsulfinyl]phenyl]sulfinylprop-2-enoxy]oxan-2-yl]methyl acetate 在 间氯过氧苯甲酸 、 3-氯苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Synthesis and biological testing of thioalkane- and thioarene-spaced bis-β-d-glucopyranosides

  摘要：

  A three-step synthesis of bis-beta-D-glucopyranosides containing thioalkane or thioarene spacers of different length and flexibility is described. The key-step reaction allows an easy modulation of final saccharidic products so that a library of molecules with different glycosidic residues and spacers can be obtained. Two of the new thioarene-spaced bis-beta-D-glucopyranosides endow with a specific cytotoxic potential. A more detailed investigation of one of the two compounds ascertains that this effect is attributable to induction of cell death by apoptosis. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.010
• 作为产物：
  描述：

  1,3-Bis(hydroxysulfanyl)benzene 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[3-[3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyprop-1-en-2-ylsulfinyl]phenyl]sulfinylprop-2-enoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Sulfenic acid – derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells

  摘要：

  This article examines the effects of some glycoconjugated disulfides and sulfoxides on red blood cells (RBCs). Compounds under study show sugar units connected directly or through a benzene platform, and have been obtained following synthetic pathways based on the sulfenic acid chemistry. In order to evaluate the relationship between the structural features of the thioglycoconjugates under investigation and their potential biological activity, we were interested in assessing both the cytotoxicity and hemolytic activity produced on human RBCs by overnight exposition to the thioglycoconjugates. The absence of both cytotoxic effect and hemolysis produced by the tested compounds on erythrocytes supports the rational design of hemocompatible molecules for biomedical applications.[GRAPHICS].

  DOI：

  10.1080/17415993.2013.778259

文献信息

• Synthesis and biological testing of thioalkane- and thioarene-spaced bis-β-d-glucopyranosides
  作者：Maria C. Aversa、Anna Barattucci、Paola Bonaccorsi、Francesca Marino-Merlo、Antonio Mastino、Maria T. Sciortino

  DOI：10.1016/j.bmc.2009.01.010

  日期：2009.2

  A three-step synthesis of bis-beta-D-glucopyranosides containing thioalkane or thioarene spacers of different length and flexibility is described. The key-step reaction allows an easy modulation of final saccharidic products so that a library of molecules with different glycosidic residues and spacers can be obtained. Two of the new thioarene-spaced bis-beta-D-glucopyranosides endow with a specific cytotoxic potential. A more detailed investigation of one of the two compounds ascertains that this effect is attributable to induction of cell death by apoptosis. (c) 2009 Elsevier Ltd. All rights reserved.
• Sulfenic acid – derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells
  作者：Paola Bonaccorsi、Maria Chiara Aversa、Anna Barattucci、Teresa Papalia、Agata Torre、Francesca Trischitta、Caterina Faggio

  DOI：10.1080/17415993.2013.778259

  日期：2013.12.1

  This article examines the effects of some glycoconjugated disulfides and sulfoxides on red blood cells (RBCs). Compounds under study show sugar units connected directly or through a benzene platform, and have been obtained following synthetic pathways based on the sulfenic acid chemistry. In order to evaluate the relationship between the structural features of the thioglycoconjugates under investigation and their potential biological activity, we were interested in assessing both the cytotoxicity and hemolytic activity produced on human RBCs by overnight exposition to the thioglycoconjugates. The absence of both cytotoxic effect and hemolysis produced by the tested compounds on erythrocytes supports the rational design of hemocompatible molecules for biomedical applications.[GRAPHICS].