1,4-di-(4'-O-acetyl-3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-1,4-butanediol | 693785-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-(4'-O-acetyl-3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-1,4-butanediol
• 英文别名: 2,2,2-trifluoro-N-[(2S,3R,4S,6R)-3-hydroxy-6-[4-[(2R,4S,5R,6S)-5-hydroxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxybutoxy]-2-methyloxan-4-yl]acetamide
• CAS: 693785-06-7
• 化学式: C₂₀H₃₀F₆N₂O₈
• 分子量: 540.457
• InChiKey: JVNFOIYFBYYQAE-UFTFSBDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,4-di-(4'-O-acetyl-3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-1,4-butanediol 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以21.4 mg的产率得到1,4-di-(3'-amido-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-1,4-butanediol
  参考文献：
  名称：

  Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties

  摘要：

  The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C-2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.013
• 作为产物：
  描述：

  1,4-di-(3'-trifluoroacetamido-4'-O-acetyl-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-2-butene-1,4-diol 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以188 mg的产率得到1,4-di-(4'-O-acetyl-3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranoside)-1,4-butanediol
  参考文献：
  名称：

  Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties

  摘要：

  The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C-2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.013