isopropyl 2-azido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside | 143996-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2-azido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside
• CAS: 143996-35-4
• 化学式: C₁₂H₂₁N₃O₅
• 分子量: 287.316
• InChiKey: OBPFERFJROCBLI-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  isopropyl 2-azido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside 在 草酰氯 、 4-甲基苯磺酸吡啶 、 potassium tri-sec-butyl-borohydride 、 二甲基亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 生成 isopropyl 2-azido-2,6-dideoxy-7-C-(2-furyl)-3,4-O-isopropylidene-D-glycero-β-D-galactoheptopyranoside
  参考文献：
  名称：

  New convenient synthesis of tunicamine

  摘要：

  A synthesis of tunicamine, the eleven-carbon atom sugar component of tunicamycin antibiotics, was described. The synthesis started from a derivative of 2-azido-2-deoxy-D-galactose (11) which was condensed with a furfuryl alcohol moiety. Achmatowicz-type transformation of this moiety to allofuranose system yielded a derivative of tunicamine. The synthesis required 11 steps and yielded 27 in 5.4% yield (from 11) and with good stereoselectivity.

  DOI：

  10.1016/s0040-4020(01)89859-8
• 作为产物：
  描述：

  (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-5-azido-6-isopropoxytetrahydro-2H-pyran-3,4-diyl diacetate 在 吡啶 、 copper(I) sulfate 、 potassium hydrogencarbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 28.0h， 生成 isopropyl 2-azido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  New convenient synthesis of tunicamine

  摘要：

  A synthesis of tunicamine, the eleven-carbon atom sugar component of tunicamycin antibiotics, was described. The synthesis started from a derivative of 2-azido-2-deoxy-D-galactose (11) which was condensed with a furfuryl alcohol moiety. Achmatowicz-type transformation of this moiety to allofuranose system yielded a derivative of tunicamine. The synthesis required 11 steps and yielded 27 in 5.4% yield (from 11) and with good stereoselectivity.

  DOI：

  10.1016/s0040-4020(01)89859-8