1,4-di-(3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-ribo-hexopyranosyl)-1,4-butanediol | 467431-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-(3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-ribo-hexopyranosyl)-1,4-butanediol
• CAS: 467431-86-3
• 化学式: C₂₀H₃₀F₆N₂O₈
• 分子量: 540.457
• InChiKey: JVNFOIYFBYYQAE-NXIAIJKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  135.58
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,4-di-(3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-ribo-hexopyranosyl)-1,4-butanediol 在 platinum(IV) oxide 、 Grubbs catalyst first generation 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 64.0h， 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：

  4-O-acetyl-3-azido-2,3,6-trideoxy-L-hexopyranose 在 platinum(IV) oxide 、 Grubbs catalyst first generation lithium aluminium tetrahydride 、 Dowex 50 (H+) resin 、 氢气 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 32.0h， 生成 1,4-di-(3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-ribo-hexopyranosyl)-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

文献信息

• Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties
  作者：Andreas Kirschning、Guang-wu Chen、Janis Jaunzems、Martin Jesberger、Markus Kalesse、Meike Lindner

  DOI：10.1016/j.tet.2004.02.013

  日期：2004.4

  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.