(5R)-2,3,6-tri-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 1159645-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-2,3,6-tri-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS: 1159645-91-6
• 化学式: C₄₂H₅₆O₁₃
• 分子量: 768.899
• InChiKey: ADKNNLHULKMOIF-BXQUIPQISA-N

物化性质

• 沸点：
  806.1±65.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  55.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  130.99
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (5R)-2,3,6-tri-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 水 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以72%的产率得到2,3,6-tri-O-benzyl-D-xylo-aldohexose-5-ulose
  参考文献：
  名称：

  Toward the synthesis of fine chemicals from lactose: preparation of d-xylo and l-lyxo-aldohexos-5-ulose derivatives

  摘要：

  The transformation of (5R)-2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranosyl-(1 -> 4)-2,3:5,6-di-O-iso-propylidene-aldehydo-D-glucose dimethyl acetal (8) into partially protected derivatives of D-xylo- and L-lyxo-aldohexos-5-ulose has been reported, applying appropriate epimerisation methods to its 3'-O- and 4'-O-protected alcoholic derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.014
• 作为产物：
  描述：

  (5R)-2,3,6-tri-O-benzyl-5-C-methoxy-α-L-arabino-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 tetra-n-propylammonium perruthenate. 、 N-甲基吗啉氧化物 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 5.5h， 以64%的产率得到(5R)-2,3,6-tri-O-benzyl-5-C-methoxy-β-D-xylo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Toward the synthesis of fine chemicals from lactose: preparation of d-xylo and l-lyxo-aldohexos-5-ulose derivatives

  摘要：

  The transformation of (5R)-2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranosyl-(1 -> 4)-2,3:5,6-di-O-iso-propylidene-aldehydo-D-glucose dimethyl acetal (8) into partially protected derivatives of D-xylo- and L-lyxo-aldohexos-5-ulose has been reported, applying appropriate epimerisation methods to its 3'-O- and 4'-O-protected alcoholic derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.014