ethyl 3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranoside
• 英文别名: (2R,3S,4R)-6-ethoxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• 化学式: C₂₉H₃₄O₅
• 分子量: 462.586
• InChiKey: AOZCHQWQOBKXER-ZTTQFBNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 乙醇 在 三氟甲磺酸 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到ethyl 3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranoside
  参考文献：
  名称：

  亲核试剂与3,4,6-Tri- O-苄基-d-葡聚糖-TfOH- n - Bu 4 NI反应体系中反应性中间体的反应

  摘要：

  形成在3,4,6-三-独特的反应性中间ö苄基d -glucal-TfOH（三氟甲磺酸） - ñ -Bu 4 NI反应体系（在二氯甲烷中）与亲核试剂在一个区域选择性和立体选择性的方式反应。这些选择性导致了迄今未知的化合物，例如在有碘离子作为亲核试剂的情况下获得的苄基4,6-二-O-苄基-2,3-二脱氧-3-碘-α-吡喃葡萄糖苷。相应的2-脱氧α-糖苷仅在与羟基亲核试剂的相应反应中获得。

  DOI：

  10.1081/car-120026596

文献信息

• Erosion of Stereochemical Control with Increasing Nucleophilicity: <i>O</i>-Glycosylation at the Diffusion Limit
  作者：Matthew G. Beaver、K. A. Woerpel

  DOI：10.1021/jo902222a

  日期：2010.2.19

  Nucleophilic substitution reactions of 2-deoxyglycosyl donors indicated that the reactivity of the oxygen nucleophile has a significant impact on stereoselectivity. Employing ethanol as the nucleophile resulted in a 1:1 (alpha:beta) ratio of diastereomers under S(N)1-like reaction conditions. Stercoselective formation of the 2-deoxy-alpha-O-glycoside was only observed when weaker nucleophiles, such as trifluoroethanol, were employed. The lack of stercoselectivity observed in reactions of common oxygen nucleophiles can be attributed to reaction rates of the stereochemistry-determining step that approach the diffusion limit. In this scenario, both faces of the prochiral oxocarbenium ion are subject to nucleophilic addition to afford a statistical mixture of diastercomeric products. Control experiments confirmed that all nucleophilic substitution reactions were performed under kinetic control.
• Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6‐Tri‐<i>O</i>‐benzyl‐<scp>d</scp>‐glucal–TfOH–<i>n</i>‐Bu₄NI Reaction System
  作者：Idil Kasuto Kelson、Ben‐Ami Feit

  DOI：10.1081/car-120026596

  日期：2003.12.31

  unique reactive intermediate formed in the 3,4,6‐tri‐O‐benzyl‐d‐glucal–TfOH (triflic acid)–n‐Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio‐ and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6‐di‐O‐benzyl‐2,3‐dideoxy‐3‐iodo‐α‐glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The

  形成在3,4,6-三-独特的反应性中间ö苄基d -glucal-TfOH（三氟甲磺酸） - ñ -Bu 4 NI反应体系（在二氯甲烷中）与亲核试剂在一个区域选择性和立体选择性的方式反应。这些选择性导致了迄今未知的化合物，例如在有碘离子作为亲核试剂的情况下获得的苄基4,6-二-O-苄基-2,3-二脱氧-3-碘-α-吡喃葡萄糖苷。相应的2-脱氧α-糖苷仅在与羟基亲核试剂的相应反应中获得。