allyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside | 693784-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside
• 英文别名: N-[(2S,3S,4S,6S)-3-hydroxy-2-methyl-6-prop-2-enoxyoxan-4-yl]acetamide
• CAS: 693784-88-2
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: GCUMISLQELKPJN-DMLMCSCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 25.0h， 生成
  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 盐酸 、 Dowex 50 [H⁽¹⁺⁾-form)] 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 allyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside
  参考文献：
  名称：

  源自l-柔红胺的间隔连接的新二糖的合成

  摘要：

  新颖头对磁头隔离联bisdaunosamine同二聚体的制备8，15和18进行说明。通过使用甲硅烷基糖苷5作为糖基供体的单甲硅烷基化的1，4-丁二醇9的双糖基化来实现合成。备选地，烯丙基糖苷α- 11，特别是α- 12的烯烃复分解构成了朝向8及其不饱和衍生物15的第二条途径，而烯丙基糖苷11和12的交叉复分解获得了不对称的二聚体18。

  DOI：

  10.1016/s0040-4039(99)00862-x

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.
• Syntheses of spacer-linked neodisaccharides derived from l-daunosamine
  作者：Andreas Kirschning、Guang-wu Chen

  DOI：10.1016/s0040-4039(99)00862-x

  日期：1999.6

  The preparation of novel head-to-head spacer-linked bisdaunosamine homodimers 8, 15 and 18 is described. The synthesis is achieved by double glycosylation of monosilylated 1,4-butanediol 9 using silyl glycoside 5 as glycosyl donor. Alternatively, olefin metathesis of allyl glycosides α-11 and particularly of α-12 constitutes a second route toward 8 and its unsaturated derivative 15 while non symmetrical

  新颖头对磁头隔离联bisdaunosamine同二聚体的制备8，15和18进行说明。通过使用甲硅烷基糖苷5作为糖基供体的单甲硅烷基化的1，4-丁二醇9的双糖基化来实现合成。备选地，烯丙基糖苷α- 11，特别是α- 12的烯烃复分解构成了朝向8及其不饱和衍生物15的第二条途径，而烯丙基糖苷11和12的交叉复分解获得了不对称的二聚体18。