5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose | 956411-31-7

• 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: 5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose
• 英文别名: [(3aR,5S,6S,6aR)-5-(acetyloxymethyl)-6-(methoxycarbonylamino)-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 956411-31-7
• 化学式: C₂₀H₂₅NO₉
• 分子量: 423.42
• InChiKey: VUIHLAIGZHEIHR-MJEZEWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-3-methoxycarbonylamino-α-D-xylofuranose 、 5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-3-methoxycarbonylamino-β-D-xylofuranose
  参考文献：
  名称：

  The efficient preparation of α-substituted serine scaffolds as the chiral building blocks for the synthesis of SPT inhibitors

  摘要：

  An efficient stereoselective synthesis of unusual substituted serine synthons 7, 10, 12 is reported. It was shown that highly functionalized furanose 6 has the suitable structure for further synthetic manipulations toward the inhibitors of SPT. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.08.019
• 作为产物：
  描述：

  5-O-(tert-butyldimethylsilyl)-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose 3-C-carbaldehyde 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.58h， 生成 5-O-acetyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-3-methoxycarbonylamino-α-D-xylofuranose
  参考文献：
  名称：

  The efficient preparation of α-substituted serine scaffolds as the chiral building blocks for the synthesis of SPT inhibitors

  摘要：

  An efficient stereoselective synthesis of unusual substituted serine synthons 7, 10, 12 is reported. It was shown that highly functionalized furanose 6 has the suitable structure for further synthetic manipulations toward the inhibitors of SPT. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.08.019