methyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosid)uronate | 29600-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosid)uronate
• 英文别名: Methyl-<2,3-di-O-benzyl-α-D-galactopyranosid>-uronsaeure-methylester；methyl (2S,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 29600-82-6
• 化学式: C₂₂H₂₆O₇
• 分子量: 402.444
• InChiKey: RIOSPUQZLPCUNG-QWPXSNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosid)uronate 在 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum

  摘要：

  Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely alpha-D-GalA-(1 -> 2)-alpha-L-Rha(1 -> 4)-beta-D-GalA-OC3H7 (1), alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 4)-beta-D-GalA-OC3H7 (2), alpha-D-GalA-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-OC3H7 (3), alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (4), and alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (5), which are relevant to the fragments of the rhamnogalacturonan of Nerium indicum, were concisely synthesized. The syntheses feature highly stereoselective formation of the alpha-D-GalA-linkage with GalA N-phenyltrifluoroacetimidates as donors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.008
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-galactopyranoside 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 四丁基碘化铵 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosid)uronate
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum

  摘要：

  Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely alpha-D-GalA-(1 -> 2)-alpha-L-Rha(1 -> 4)-beta-D-GalA-OC3H7 (1), alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 4)-beta-D-GalA-OC3H7 (2), alpha-D-GalA-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-OC3H7 (3), alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (4), and alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (5), which are relevant to the fragments of the rhamnogalacturonan of Nerium indicum, were concisely synthesized. The syntheses feature highly stereoselective formation of the alpha-D-GalA-linkage with GalA N-phenyltrifluoroacetimidates as donors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.008

文献信息

• Synthesis of two repeat units corresponding to the backbone of the pectic polysaccharide rhamnogalacturonan I
  作者：Dominic Reiffarth、Kerry B. Reimer

  DOI：10.1016/j.carres.2007.10.030

  日期：2008.2

  A tetrasaccharide corresponding to a sequence of the rhamnogalacturonan I backbone has been synthesized. This synthesis relies on only two protected monosaccharides and proceeds through a common disaccharide intermediate. Synthesis of this tetrasaccharide has been designed to allow for the addition of branching elements at the 4-positions of the rhamnosyl units, or further chain elongation at the 2-position. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum
  作者：Yuyong Ma、Xin Cao、Biao Yu

  DOI：10.1016/j.carres.2013.05.008

  日期：2013.8

  Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely alpha-D-GalA-(1 -> 2)-alpha-L-Rha(1 -> 4)-beta-D-GalA-OC3H7 (1), alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 4)-beta-D-GalA-OC3H7 (2), alpha-D-GalA-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-OC3H7 (3), alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (4), and alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (5), which are relevant to the fragments of the rhamnogalacturonan of Nerium indicum, were concisely synthesized. The syntheses feature highly stereoselective formation of the alpha-D-GalA-linkage with GalA N-phenyltrifluoroacetimidates as donors. (c) 2013 Elsevier Ltd. All rights reserved.