[(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol | 354113-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol
• 英文别名: [(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(naphthalen-2-ylmethoxy)-3-phenylmethoxyoxan-2-yl]methanol
• CAS: 354113-98-7
• 化学式: C₃₆H₃₆O₆
• 分子量: 564.678
• InChiKey: OHNNCHLWTXXLSE-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-甲氧基氯苄 、 [(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran
  参考文献：
  名称：

  Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ

  摘要：

  The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00563-9
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 以65%的产率得到[(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol
  参考文献：
  名称：

  Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ

  摘要：

  The selective cleavage of the PMB (4-methoxybenzyl) group in the presence of the NAP (2-naphthylmethyl) group was achieved using CAN with a range of mono-saccharides. The NAP group can then be removed selectively in the presence of a benzyl group using DDQ. This provides a strategy for sequential deprotection of hydroxyl groups. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00563-9