(5S)-3-O-benzyl-6-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose

• 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: (5S)-3-O-benzyl-6-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• 英文别名: (1S)-1-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-dimethoxyphosphorylethanol
• 化学式: C₁₈H₂₇O₈P
• 分子量: 402.381
• InChiKey: BGDRRFINWXJHDR-QFXBJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 lithium aluminium tetrahydride 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 pyridinium chlorochromate 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 (5S)-3-O-benzyl-6-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose
  参考文献：
  名称：

  Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

  摘要：

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00235-0

文献信息

• Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)
  作者：Tadashi Hanaya、Ken-ichi Sugiyama、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.1016/s0008-6215(03)00235-0

  日期：2003.7

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.