methyl (allyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosid)uronate | 1000375-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (allyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosid)uronate
• 英文别名: methyl (2S,3R,4S,5R,6S)-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)-6-prop-2-enoxyoxane-2-carboxylate
• CAS: 1000375-90-5
• 化学式: C₃₂H₃₆O₈
• 分子量: 548.633
• InChiKey: WNTQSGIHHKFWGJ-UNOUFDOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (allyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosid)uronate 在 palladium dichloride sodium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 、 methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-D-galactopyranuronate
  参考文献：
  名称：

  Allyl deprotection of galacturonic acid derivatives: mechanistic aspects of mercuric-catalyzed prop-1-enyl acetal cleavage

  摘要：

  Different deallylation methods were assayed for selective deprotection of allyl galactopyranosiduronic acid derivatives. A two-step procedure using DABCO and (Ph3P)(3)RhCl followed by mercuric-assisted cleavage gave quantitative yields. Reaction in the presence of [O-18]water allowed us to obtain evidence about the mechanism of prop-l-enyl cleavage. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.019
• 作为产物：
  描述：

  allyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosiduronic acid 、 碘甲烷 在 四丁基碘化铵 、 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以91%的产率得到methyl (allyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosid)uronate
  参考文献：
  名称：

  Allyl deprotection of galacturonic acid derivatives: mechanistic aspects of mercuric-catalyzed prop-1-enyl acetal cleavage

  摘要：

  Different deallylation methods were assayed for selective deprotection of allyl galactopyranosiduronic acid derivatives. A two-step procedure using DABCO and (Ph3P)(3)RhCl followed by mercuric-assisted cleavage gave quantitative yields. Reaction in the presence of [O-18]water allowed us to obtain evidence about the mechanism of prop-l-enyl cleavage. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.08.019

文献信息

• Allyl deprotection of galacturonic acid derivatives: mechanistic aspects of mercuric-catalyzed prop-1-enyl acetal cleavage
  作者：Maximilien Barbier、Eric Grand、José Kovensky

  DOI：10.1016/j.carres.2007.08.019

  日期：2007.12

  Different deallylation methods were assayed for selective deprotection of allyl galactopyranosiduronic acid derivatives. A two-step procedure using DABCO and (Ph3P)(3)RhCl followed by mercuric-assisted cleavage gave quantitative yields. Reaction in the presence of [O-18]water allowed us to obtain evidence about the mechanism of prop-l-enyl cleavage. (c) 2007 Elsevier Ltd. All rights reserved.