(3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol | 1005763-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
• 英文别名: 2,6-anhydro-4,5,7-tri-O-benzyl-1-deoxy-2ξ-D-gluco-heptitol
• CAS: 1005763-00-7
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: HTBCIOACXYNFLJ-VXGYKJTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 D-glucopyransoe
  参考文献：
  名称：

  The exo-deoxoanomeric effect in the conformational preferences of C-glycosides

  摘要：

  Rotational studies of a series of beta-D-C-glycopyranosides were carried out by CD and NMR spectroscopy. The populations around the C-glycosidic bond were strongly dependent on the structure of the C-aglycon, the exo-syn rotamer population increasing with the degree of substitution on the C-aglycon. The hydroxymethyl group populations also showed dependence on the aglycon, although to a lesser degree; its gt rotamer smoothly increases with the substitution on the aglycon. These rotational preferences, together with the experimentally observed correlations between H-1 and C-13 NMR chemical shifts and the structural nature of the C-aglycon, point to a stercoelectronic sigma(CH)-sigma*(CO) effect (hyperconjugation) directly involved in the rotation around the pseudo-glycosidic bond and indirectly around the C5-C6 bond (hydroxymethyl group). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.007
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 二甲基二环氧乙烷 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  The exo-deoxoanomeric effect in the conformational preferences of C-glycosides

  摘要：

  Rotational studies of a series of beta-D-C-glycopyranosides were carried out by CD and NMR spectroscopy. The populations around the C-glycosidic bond were strongly dependent on the structure of the C-aglycon, the exo-syn rotamer population increasing with the degree of substitution on the C-aglycon. The hydroxymethyl group populations also showed dependence on the aglycon, although to a lesser degree; its gt rotamer smoothly increases with the substitution on the aglycon. These rotational preferences, together with the experimentally observed correlations between H-1 and C-13 NMR chemical shifts and the structural nature of the C-aglycon, point to a stercoelectronic sigma(CH)-sigma*(CO) effect (hyperconjugation) directly involved in the rotation around the pseudo-glycosidic bond and indirectly around the C5-C6 bond (hydroxymethyl group). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.007

文献信息

• New insights into the conformational properties of α-C-glucosides
  作者：Carlos Mayato、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.tetasy.2007.11.002

  日期：2007.11

  A series of alkyl α-d-C-glucopyranosides were synthesized and their conformational properties analyzed by CD and NMR spectroscopy. The conformational analysis revealed that the hydroxymethyl group populations (torsion angle ω, O1–C1–C2–O2) and those around the C-glucopyranosidic bond (torsion angle Φ; O2–C6–C7–C8) depend on the structural nature of the C-aglycon. The gt and the exo–syn populations

  合成了一系列烷基α-d- C-吡喃葡萄糖苷，并通过CD和NMR光谱分析了它们的构象性质。构象分析表明，羟甲基基团（扭转角ω，O1-C1-C2-O2）和C-吡喃葡萄糖苷键周围的分子（扭转角Φ； O2-C6-C7-C8）取决于分子的结构性质。C-糖苷配基。在GT和外-顺式种群增加作为Ç -aglycon变得更加取代。这些旋转种群和质子化学位移与塔夫脱的空间参数之间的线性相关性揭示了碳的重要作用C-葡糖苷的整体构象中的β-糖苷配基。随着运动的空间位阻的增加，影响羟甲基旋转的立体电子外-脱氧异头作用变得更加重要。甲伪还进行端基异构体的旋转比较研究。
• C-Glycosides to fused polycyclic ethers
  作者：Shawn P. Allwein、Jason M. Cox、Brett E. Howard、Henry W.B. Johnson、Jon D. Rainier

  DOI：10.1016/s0040-4020(02)00057-1

  日期：2002.3

  This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.