3,4-O-Isopropyliden-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-O-Isopropyliden-D-galactopyranose
• 英文别名: 3,4-O-Isopropylidene-d-galactose；(3aS,4R,7R,7aR)-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6,7-diol
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: YEYXZTDLMVJYOR-KEWYIRBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-O-Isopropyliden-D-galactopyranose 在 吡啶 、 1,1-二氯甲醚 、 溶剂黄146 、 zinc(II) chloride 作用下， 反应 2.0h， 生成 2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride
  参考文献：
  名称：

  Expedient synthesis of a series of N-acetyllactosamines

  摘要：

  A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00485-0
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3,4-O-Isopropyliden-D-galactopyranose
  参考文献：
  名称：

  Expedient synthesis of a series of N-acetyllactosamines

  摘要：

  A series of poly-N-acetyllactosamines representative of those found on complex N-glycans was synthesized for use in the kinetic characterization of recently cloned glycosyltransferases. The syntheses involved the iterative addition of a selectively protected N-acetyllactosaminyl donor to an octyl alpha-D-mannopyranosyl-1,6-beta-mannopyranoside acceptor, followed by deprotection. In addition, non-reducing galactosyl residues were removed with beta-galactosidase to furnish GlcNAc terminated compounds. In this manner tetra- to octasaccharides were efficiently produced. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00485-0

文献信息

• Reaction of cyclic ketals with ceric ammonium nitrate in acetonitrile/water
  作者：Emiliano Manzo、Gaspare Barone、Emiliano Bedini、Alfonso Iadonisi、Lorenzo Mangoni、Michelangelo Parrilli

  DOI：10.1016/s0040-4020(01)01006-7

  日期：2002.1

  performing the hydrolysis of cyclic acetals and ketals under basic or mildly alkaline conditions by ceric ammonium nitrate (CAN) in MeCN/H2O or in 10% aq. methanol is rejected. However a role for Ce(IV) as Lewis acid is evidenced at pH 4.4. Under these conditions, which allow hydrolysis of cyclic ketals leaving glycosidic bonds unaltered, a selectivity of ketal cleavage due to steric hindrance is also

  在碱性或弱碱性条件下，通过硝酸铈铵（CAN）在MeCN / H 2 O或10％水溶液中进行环状缩醛和缩酮水解的可能性。甲醇被拒绝。然而，在pH 4.4下证明了Ce（IV）作为路易斯酸的作用。在这些条件下，允许环缩酮水解而糖苷键保持不变，还可以观察到由于空间位阻而引起的缩酮切割的选择性。当丙酮/水代替MeCN / H 2 O作为溶剂时，可获得相似的收率。
• Stereoselective Tandem Epoxidation-Alcoholysis/Hydrolysis of Glycals with Molybdenum Catalysts
  作者：Irene Marín、M. Isabel Matheu、Yolanda Díaz、Sergio Castillón

  DOI：10.1002/adsc.201000614

  日期：2010.12.17

  Molybdenum catalysts are efficient and selective catalysts for the tandem epoxidation/alcoholysis or epoxidation/hydrolysis of glucal and galactal derivatives. In glucal derivatives the selectivity is mainly controlled by the allylic substituent at position 3 of the glycal, obtaining in general the products derived from the initial formation of the α-epoxide (gluco) when this hydroxy group is protected, while

  钼催化剂是用于葡糖和半乳糖衍生物的串联环氧化/醇解或环氧化/水解的有效且选择性的催化剂。在葡糖衍生物中，选择性主要受糖基位置3上的烯丙基取代基控制，通常获得在羟基被保护时最初衍生自α-环氧化物（葡萄糖）的产物，而衍生自β的产物。 -环氧化物（甘露）主要是在未保护的情况下获得的。在半乳衍生物中，酯选择性始终很高，可以得到α-环氧化物（半乳酸酯），并且与保护基团无关。