methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside | 205192-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside
• 英文别名: [(2S,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 205192-05-8
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: MOKYEUQDXDKNDX-BIJRFUASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.17h， 生成 methyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate
  参考文献：
  名称：

  Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars

  摘要：

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.

  DOI：

  10.1002/chem.200600268
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 在 Ti(OiPr)Cl3 、 三乙基硼氢化锂 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.75h， 以73%的产率得到methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside
  参考文献：
  名称：

  宝石-二氟卡巴-D-葡萄糖的合成：进一步进行糖模仿。

  摘要：

  DOI：

  10.1002/anie.200461244

文献信息

• Synthesis of <scp>l</scp>-Pyranosides by Hydroboration of Hex-5-enopyranosides Revisited
  作者：Grzegorz Łopatkiewicz、Jacek Mlynarski

  DOI：10.1021/acs.joc.6b01243

  日期：2016.9.2

  Extensive study of the diastereoselective synthesis of l-pyranosides utilizing hydroboration of substituted exo-glucals (5-enopyranosides) obtained from d-sugars is presented. On the basis of this study we present the empirical rules describing the reaction stereoselectivity and the correlation between the yield of the l-ido product and the size of protecting groups used. Application of these guidelines

  提出了广泛的研究，利用从d-糖获得的取代的exo-葡糖醛酸（5- enopyranosides）的硼氢化方法对l- pyranosides进行非对映选择性合成。在这项研究的基础上，我们给出了描述反应立体选择性的经验法则，以及l - ido产物的收率和所用保护基团大小之间的相关性。这些准则的应用表明，甲基2,3-的硼氢化ø甲基-6-脱氧α- d -木糖-己-5-烯吡喃糖苷导致的独家形成升- IDO产品产量高。该方法可以成功地用于合成作为抗凝血药必不可少的非对映体选择性优于以前发表的协议的1-异丁烯二酸。
• Probing the Specificity of Aminoglycoside−Ribosomal RNA Interactions with Designed Synthetic Analogs
  作者：Phil B. Alper、Martin Hendrix、Pamela Sears、Chi-Huey Wong

  DOI：10.1021/ja972599h

  日期：1998.3.1

  The binding of neomycin B and related aminoglycoside antibiotics to the prokaryotic ribosomal RNA decoding region has been investigated using a recently developed surface plasmon resonance assay. A number of naturally occurring aminoglycosides containing a neamine or neamine-like substructure bind specifically to a model of the site of the ribosomal decoding region RNA. This recognition event is the

  新霉素 B 和相关氨基糖苷类抗生素与原核核糖体 RNA 解码区域的结合已使用最近开发的表面等离子体共振测定进行了研究。许多含有神经胺或神经胺样亚结构的天然氨基糖苷类与核糖体解码区 RNA 位点的模型特异性结合。这种识别事件是此类化合物抗菌活性的基础。设计并合成了一系列类似物来探索新霉素环 IV（2,6-dideoxy-2,6-diamino-β-l-idopyranose）的作用。结合结果表明，idose 环上的正电荷是体外特异性结合所必需的，不能被通过柔性接头连接的胺取代。然而，
• Synthesis of<i>gem</i>-Difluorocarba-<scp>D</scp>-glucose: A Step Further in Sugar Mimesis
  作者：Aurélie Deleuze、Candice Menozzi、Matthieu Sollogoub、Pierre Sinaÿ

  DOI：10.1002/anie.200461244

  日期：2004.12.10
• Divergent Synthesis ofL-Sugars andL-Iminosugars fromD-Sugars
  作者：Hideyo Takahashi、Tomomi Shida、Yuko Hitomi、Yoshinori Iwai、Namisa Miyama、Kazusa Nishiyama、Daisuke Sawada、Shiro Ikegami

  DOI：10.1002/chem.200600268

  日期：2006.7.24

  AbstractAn efficient divergent synthesis of L‐sugars and L‐iminosugars from D‐sugars is described. The important intermediate, δ‐hydroxyalkoxamate, prepared from D‐glucono‐/galactono‐1,5‐lactone, was cyclized under Mitsunobu conditions to give the O‐cyclized oxime compound and the N‐cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O‐/N‐cyclization of the δ‐hydroxyalkoxamate. Suitable protection at the 6‐position of δ‐hydroxyalkoxamate, derived from D‐glucono‐1,5‐lactone, afforded the corresponding O‐alkylation product alone. Thus we succeeded in applying this to the total synthesis of L‐iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D‐glucono/galactono‐1,5‐lactone into the corresponding L‐iminosugars (L‐idonolactam and L‐altronolactam) was achieved.