methyl 3-acetamido-4-allyl-2,3,6-trideoxy-β-L-lyxo-hexopyranoside | 693785-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-acetamido-4-allyl-2,3,6-trideoxy-β-L-lyxo-hexopyranoside
• 英文别名: N-[(2S,3S,4S,6S)-6-methoxy-2-methyl-3-prop-2-enoxyoxan-4-yl]acetamide
• CAS: 693785-09-0
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: IOLUGDHHMHCKAN-PDEGPIFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-acetamido-4-allyl-2,3,6-trideoxy-β-L-lyxo-hexopyranoside 在 palladium on activated charcoal 、 Grubbs catalyst first generation barium dihydroxide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 54.5h， 生成 (2S,3S,4S,6S)-3-[4-[(2S,3S,4S,6R)-4-amino-6-[4-[(2R,4S,5S,6S)-4-amino-5-[4-[(2S,3S,4S,6S)-4-amino-6-methoxy-2-methyloxan-3-yl]oxybutoxy]-6-methyloxan-2-yl]oxybutoxy]-2-methyloxan-3-yl]oxybutoxy]-6-methoxy-2-methyloxan-4-amine
  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 、 丙烯酰碘 在 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以90%的产率得到methyl 3-acetamido-4-allyl-2,3,6-trideoxy-β-L-lyxo-hexopyranoside
  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.