2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol | 160318-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol
• 英文别名: (3R,4R,5R,6R)-2-methylidene-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 160318-53-6
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: WHXFGVJISBUCFW-JUDWXZBOSA-N

物化性质

• 沸点：
  586.6±50.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 bis(β-D-glucopyranosyl)methane
  参考文献：
  名称：

  Selective radical synthesis of β- C -disaccharides

  摘要：

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01533-7
• 作为产物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose 在 sodium methylate 、 乙酸酐 、 二甲基亚砜 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 51.0h， 生成 2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-1-heptenitol
  参考文献：
  名称：

  Expedient and Versatile Formation of Novel Amino-deoxy-ketoheptuloses

  摘要：

  Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-ketohept-2-uloses could be obtained.

  DOI：

  10.1021/ol4021699

文献信息

• Claisen-Ireland rearrangement: a new route to C-glycosides
  作者：Thierry Vidal、Arnaud Haudrechy、Yves Langlois

  DOI：10.1016/s0040-4039(99)01055-2

  日期：1999.7

  A Claisen-Ireland rearrangement led to the formation of C-glycan derivatives. Azidonitration-reduction or dihydroxylation afforded gluco- and galacto-derived β-C-glycosides. Subsequent deprotonation of bicyclic lactones 16 allowed the control of the newly created asymmetric centre.

  Claisen-Ireland重排导致C-聚糖衍生物的形成。叠氮化还原或二羟基化提供了葡萄糖和半乳糖衍生的β- C-糖苷。随后双环内酯16的去质子化使得可以控制新产生的不对称中心。
• A new route to C-glycosylidene compounds mediated by olefin metathesis
  作者：Olivier Dirat、Thierry Vidal、Yves Langlois

  DOI：10.1016/s0040-4039(99)00913-2

  日期：1999.6

  Various 1-methylene glucose derivatives afforded after ring closure olefin metathesis cyclic polyethers and C-glycoside precursors.

  闭环烯烃复分解后得到的各种1-亚甲基葡萄糖衍生物环状聚醚和C-糖苷前体。
• Synthesis and spontaneous dimerization of the tri-O-benzyl derivative of ”2-keto-1-C-methylene-d-glucopyranose” (2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-d-arabino-hept-1-en-3-ulose)
  作者：Olivier R. Martin、Fang Xie

  DOI：10.1016/0008-6215(94)00191-x

  日期：1994.11
• Diastereoselective access to <i>C</i>,<i>C</i>-glycosyl amino acids <i>via</i> iron-catalyzed, auxiliary-enabled MHAT coupling
  作者：Mylène Lang、Damien Tardieu、Benoit Pousse、Philippe Compain、Nicolas Kern

  DOI：10.1039/d3cc06249j

  日期：2024.3.14

  Novel C,C-glycosyl amino acids were accessed by means of an iron-catalyzed hydrogen atom transfer sequence. Crucially, two-fold diastereocontrol could be achieved in the ‘matched’ coupling of exo-d-glycals with an enantiopure dehydroalanine acceptor.
• Expedient and Versatile Formation of Novel Amino-deoxy-ketoheptuloses
  作者：Yevgeniy Leshch、Anna Jacobsen、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol4021699

  日期：2013.10.4

  Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-ketohept-2-uloses could be obtained.