(2S,3S)-2,3-bis(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-1-(3,4-dimethoxybenzyloxy)butane | 1337562-47-6

• 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: (2S,3S)-2,3-bis(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-1-(3,4-dimethoxybenzyloxy)butane
• 英文别名: tert-butyl-[(2S,3S)-4-[(3,4-dimethoxyphenyl)methoxy]-2,3-bis(phenylmethoxy)butoxy]-diphenylsilane
• CAS: 1337562-47-6
• 化学式: C₄₃H₅₀O₆Si
• 分子量: 690.952
• InChiKey: YMAPLWFXQOYDNZ-COCZKOEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-bis(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-1-(3,4-dimethoxybenzyloxy)butane 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(+)-(2S,3S)-2,3-bis(benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)butan-1-ol
  参考文献：
  名称：

  Effective chemoselective deprotection of 3,4-dimethoxybenzyl (3,4DMB) ethers in the presence of benzyl and p-methoxybenzyl (PMB) ethers by phenyliodine(III) bis(trifluoroacetate) (PIFA)

  摘要：

  In this Letter, a selective deprotection of the alcohol protecting 3,4-dimethoxybenzyl ((DMB)-D-3,4) group is described. The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) is found to be an efficient reagent for the chemoselective deprotection of (DMB)-D-3,4 ethers in the presence of benzyl, p-methoxybenzyl, methoxymethyl, tert-butyldimethylsilyl, and tert-butyldiphenylsilyl ethers under mild conditions. This is the first example of the selective deprotection of the (DMB)-D-3,4 group from a hydroxy group with PIFA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.049
• 作为产物：
  描述：

  (+)-(2S,3S)-2,3-bis(benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)butan-1-ol 、 3,4-二甲氧基苄氯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以93%的产率得到(2S,3S)-2,3-bis(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-1-(3,4-dimethoxybenzyloxy)butane
  参考文献：
  名称：

  Effective chemoselective deprotection of 3,4-dimethoxybenzyl (3,4DMB) ethers in the presence of benzyl and p-methoxybenzyl (PMB) ethers by phenyliodine(III) bis(trifluoroacetate) (PIFA)

  摘要：

  In this Letter, a selective deprotection of the alcohol protecting 3,4-dimethoxybenzyl ((DMB)-D-3,4) group is described. The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) is found to be an efficient reagent for the chemoselective deprotection of (DMB)-D-3,4 ethers in the presence of benzyl, p-methoxybenzyl, methoxymethyl, tert-butyldimethylsilyl, and tert-butyldiphenylsilyl ethers under mild conditions. This is the first example of the selective deprotection of the (DMB)-D-3,4 group from a hydroxy group with PIFA. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.049