1,4-bis (3'-acetamido-4'-O-allyl-2',3',6'-trideoxy-α-L-lyxo-hexopyranosyl)-1,4-butanediol | 693785-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis (3'-acetamido-4'-O-allyl-2',3',6'-trideoxy-α-L-lyxo-hexopyranosyl)-1,4-butanediol
• 英文别名: N-[(2S,3S,4S,6R)-6-[4-[(2R,4S,5S,6S)-4-acetamido-6-methyl-5-prop-2-enoxyoxan-2-yl]oxybutoxy]-2-methyl-3-prop-2-enoxyoxan-4-yl]acetamide
• CAS: 693785-15-8
• 化学式: C₂₆H₄₄N₂O₈
• 分子量: 512.644
• InChiKey: LTUMBPHNOWOBSD-XKBDDXECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-acetamido-4-allyl-2,3,6-trideoxy-β-L-lyxo-hexopyranoside 、 1,4-bis (3'-acetamido-4'-O-allyl-2',3',6'-trideoxy-α-L-lyxo-hexopyranosyl)-1,4-butanediol 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 生成 1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-2-butene-1,4-diol 、 N-{(2S,3S,4S,6R)-6-[4-((2R,4S,5S,6S)-4-Acetylamino-5-allyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butoxy]-3-[(Z)-4-((2S,3S,4S,6S)-4-acetylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-but-2-enyloxy]-2-methyl-tetrahydro-pyran-4-yl}-acetamide 、 N,N'-((2S,2'S,3S,3'S,4S,4'S,6S,6'S)-(((((2S,2'S,3S,3'S,4S,4'S,6R,6'R)-(butane-1,4-diylbis(oxy))bis(4-acetamido-2-methyltetrahydro-2H-pyran-6,3-diyl))bis(oxy))bis(but-2-ene-4,1-diyl))bis(oxy))bis(6-methoxy-2-methyltetrahydro-2H-pyran-3,4-diyl))diacetamide
  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：

  N-Acetyl-L-daunosamine 在 Grubbs catalyst first generation 、 Dowex-50 (H+ form) 吡啶 、 4-二甲氨基吡啶 、 silver(l) oxide 作用下， 以 乙腈 、 苯 为溶剂， 反应 26.5h， 生成 1,4-bis (3'-acetamido-4'-O-allyl-2',3',6'-trideoxy-α-L-lyxo-hexopyranosyl)-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