1,4-bis[allyl 3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranos-4'-yl]-1,4-butanediol | 467431-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1,4-bis[allyl 3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranos-4'-yl]-1,4-butanediol
• CAS: 467431-63-6
• 化学式: C₂₆H₃₈F₆N₂O₈
• 分子量: 620.587
• InChiKey: RFGICUKSLPMOON-CLPXVCJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  113.58
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,4-bis[allyl 3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranos-4'-yl]-1,4-butanediol 在 Grubbs catalyst first generation sodium hydroxide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 29.0h， 生成 (E)-(1R,8R,10S,11R,18R,19S,22S,23S)-10,19-Dimethyl-2,7,9,12,17,20-hexaoxa-tricyclo[16.2.2.2^8,11]tetracos-4-ene-22,23-diamine
  参考文献：
  名称：

  First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides

  摘要：

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.

  DOI：

  10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p
• 作为产物：
  描述：

  (E/Z)-1,4-bis[tert-butyldimethylsilyl 3'-trifluoroacetamido-2',3',6'-trideoxy-β-L-arabino-hexopyranos-4'-yl]-2-butene-1,4-diol 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 1,4-bis[allyl 3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-arabino-hexopyranos-4'-yl]-1,4-butanediol
  参考文献：
  名称：

  First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides

  摘要：

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.

  DOI：

  10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p