2,2,2-trifluoro-N-[(2S,3R,4R,6R)-2-methyl-6-[4-[(2R,4R,5R,6S)-6-methyl-5-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxybutoxy]-3-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxyoxan-4-yl]acetamide | 467432-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trifluoro-N-[(2S,3R,4R,6R)-2-methyl-6-[4-[(2R,4R,5R,6S)-6-methyl-5-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxybutoxy]-3-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxyoxan-4-yl]acetamide
• CAS: 467432-00-4
• 化学式: C₄₂H₅₈F₁₂N₄O₁₄
• 分子量: 1070.92
• InChiKey: DAHJBSKQWCFQKE-SULTUEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  72
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  209
• 氢给体数：
  4
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-[(2S,3R,4R,6R)-2-methyl-6-[4-[(2R,4R,5R,6S)-6-methyl-5-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxybutoxy]-3-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxyoxan-4-yl]acetamide 在 platinum(IV) oxide 、 Grubbs catalyst first generation 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 40.0h， 生成
  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：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 platinum(IV) oxide 、 Grubbs catalyst first generation lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Montmorillonite K 10 clay 、 Montmorillonite K 10 、 水 、 氢气 、 三乙胺 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 77.0h， 生成 2,2,2-trifluoro-N-[(2S,3R,4R,6R)-2-methyl-6-[4-[(2R,4R,5R,6S)-6-methyl-5-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxybutoxy]-3-[(2S,4S,5R,6S)-6-methyl-5-prop-2-enoxy-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]oxyoxan-4-yl]acetamide
  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

文献信息

• First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides
  作者：Guang-wu Chen、Andreas Kirschning

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

  日期：2002.6.17

  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.