1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-1,4-butanediol | 693785-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-1,4-butanediol
• 英文别名: N-[(2S,3S,4S,6S)-3-[4-[(2S,3S,4S,6S)-4-acetamido-6-methoxy-2-methyloxan-3-yl]oxybutoxy]-6-methoxy-2-methyloxan-4-yl]acetamide
• CAS: 693785-11-4
• 化学式: C₂₂H₄₀N₂O₈
• 分子量: 460.568
• InChiKey: NFPGZJSETPTAAC-CALRDUFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-1,4-butanediol 在 barium dihydroxide 、 Amberlite IRA-900 (OH^(1-) form) 作用下， 以 水 为溶剂， 反应 48.5h， 以85%的产率得到1,4-bis (methyl-3'-amino-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yl)-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：

  methyl N-acetyl-β-L-daunosamide 在 palladium on activated charcoal 、 Grubbs catalyst first generation 氢气 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 25.0h， 生成 1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-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

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.