allyl 4-O-acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-β-L-ribo-hexopyranoside | 693784-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 4-O-acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-β-L-ribo-hexopyranoside
• 英文别名: [(2S,3S,4R,6S)-4-methoxy-2,4-dimethyl-6-prop-2-enoxyoxan-3-yl] acetate
• CAS: 693784-87-1
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: STPYJAVTNRIBSJ-XYJRDEOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 4-O-acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-β-L-ribo-hexopyranoside 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 1,4-di-(4'-O-acetyl-2',6'-dideoxy-3'-C-methyl-3'-O-methyl-β-L-ribo-hexopyranosyl)-2-butene-1,4-diol
  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：

  L-cladinose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 反应 2.08h， 生成 allyl 4-O-acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-β-L-ribo-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