methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate | 1448254-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate
• 英文别名: methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosyluronate N-phenyl trifluoroacetimidate
• CAS: 1448254-97-4
• 化学式: C₃₁H₃₀F₃NO₈
• 分子量: 601.576
• InChiKey: CPOPZGDYTISDHE-PYSYPBHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101.88
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate 、 methyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 以99%的产率得到methyl (methyl 2,3-di-O-benzyl-4-O-acetyl-α-D-galactopyranosyluronate)-(1→2)-3,4-di-O-benzyl-β-L-rhamnopyranosyl-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosyl)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
• 作为产物：
  描述：

  在 四丁基碘化铵 、 potassium carbonate 、 potassium hydrogencarbonate 、 palladium dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 21.17h， 生成 methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate
  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

• Efficient synthesis of building blocks for branched rhamnogalacturonan I fragments
  作者：Amayak Pogosyan、Andreas Gottwald、Dirk Michalik、Hans-Ulrich Endress、Christian Vogel

  DOI：10.1016/j.carres.2013.06.019

  日期：2013.10

  syl)-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (5) was synthesized under Helferich conditions. Module 5 was converted to 2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranosyl bromide (8) which was then coupled with methyl (allyl 2,3-di-O-benzyl-β-d-galactopyranosid)uronate (11) to provide methyl (2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→4)-(2-O

  从烯丙基2-O-乙酰基-3-O-苄基-α-1-鼠李糖吡喃糖苷（3）开始，烯丙基（2,3,4,6-四-O-苯甲酰基-β-d-吡喃并吡喃糖基）-（1→在Helferich条件下合成了4）-2-O-乙酰基-3-O-苄基-α-1-鼠李吡喃糖苷（5）。将模块5转化为2,3,4,6-四-O-苯甲酰基-β-d-吡喃半乳糖基-（1→4）-2-O-乙酰基-3-O-苄基-α-1-鼠李糖基吡喃糖基溴化物（然后将其与（8,3-烯丙基2,3-二-O-苄基-β-d-吡喃半乳糖苷）尿酸酯（11）偶联以提供甲基（2,3,4,6-四-O-苯甲酰基-β- d-半乳糖吡喃糖基）-（1→4）-（2-O-乙酰基-3-O-苄基-α-1-鼠李糖基吡喃糖基）-（1→4）-（烯丙基2,3-二-O-苄基-β -d-吡喃半乳糖苷）尿酸盐（14）。或者，将模块5转化成适合作为烯丙基的2,3,4,6-四-O-苯甲酰基-β-d-吡喃半乳糖基-（1→