2,3,4,5-tetra-O-benzyl-D-glucose propane-1,3-diyl dithioacetal | 1427016-52-1

• 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: 2,3,4,5-tetra-O-benzyl-D-glucose propane-1,3-diyl dithioacetal
• 英文别名: (2R,3R,4S,5R)-5-(1,3-dithian-2-yl)-2,3,4,5-tetrakis(phenylmethoxy)pentan-1-ol
• CAS: 1427016-52-1
• 化学式: C₃₇H₄₂O₅S₂
• 分子量: 630.869
• InChiKey: FWEOVDIWFQGEAQ-PEDCNLCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-benzyl-D-glucose propane-1,3-diyl dithioacetal 在 草酰氯 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 2.58h， 生成 2,3,4,5-tetra-O-benzyl-6-deoxy-6,6-(ethylene-1,2-dioxy)-D-glucose-propane-1,3-diyl dithioacetal
  参考文献：
  名称：

  General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars

  摘要：

  A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

  DOI：

  10.1021/jo400130p
• 作为产物：
  描述：

  2,3,4,5-tetra-O-benzyl-6-O-trityl-D-glucose propane-1,3-diyldithioacetal 在 甲醇 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到2,3,4,5-tetra-O-benzyl-D-glucose propane-1,3-diyl dithioacetal
  参考文献：
  名称：

  General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars

  摘要：

  A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

  DOI：

  10.1021/jo400130p

文献信息

• Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes
  作者：Grzegorz Witkowski、Mykhaylo A. Potopnyk、Karolina Tiara、Anna Osuch-Kwiatkowska、Sławomir Jarosz

  DOI：10.3390/molecules25153357

  日期：——

  2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure.

  2,3,4-三-O-苄基-D-吡喃木糖用作制备相应三烯的起始材料，三烯顺利环化为多羟基化的海茚，作为单一的非对映异构体。由 D-葡萄糖制备的类似三烯即使在高压下也不发生任何环化。