(2R,3S,4S,5R,6S)-2-Benzyloxymethyl-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-ol | 354114-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6S)-2-Benzyloxymethyl-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4S,5R,6S)-6-methoxy-4,5-bis(naphthalen-2-ylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 354114-04-8
• 化学式: C₃₆H₃₆O₆
• 分子量: 564.678
• InChiKey: OLBAEVPBDNBAFT-BVMCXEQJSA-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：

  (2R,3S,4S,5R,6S)-2-Benzyloxymethyl-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-ol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以75%的产率得到methyl 6-O-benzyl-α-D-galactopyranoside
  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,3S,4S,5R,6S)-2-Benzyloxymethyl-6-methoxy-3-(4-methoxy-benzyloxy)-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 为溶剂， 以78%的产率得到(2R,3S,4S,5R,6S)-2-Benzyloxymethyl-6-methoxy-4,5-bis-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-ol
  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