(2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran | 354113-95-4

• 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-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4-bis[(4-methoxyphenyl)methoxy]-6-(naphthalen-2-ylmethoxymethyl)-5-phenylmethoxyoxane
• CAS: 354113-95-4
• 化学式: C₄₁H₄₄O₈
• 分子量: 664.796
• InChiKey: PJUPQHKLCAQPJK-WEOXEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 以61%的产率得到(2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-3,4-diol
  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：

  methyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-phenylmethylene-α-D-glucopyranoside 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-(naphthalen-2-ylmethoxymethyl)-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

文献信息

• Sequential removal of the benzyl-type protecting groups PMB and NAP by oxidative cleavage using CAN and DDQ
  作者：Joseph A Wright、Jinquan Yu、Jonathan B Spencer

  DOI：10.1016/s0040-4039(01)00563-9

  日期：2001.6

  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.