2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,6-di-O-benzoyl-β-D-psicofuranoside | 1242059-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,6-di-O-benzoyl-β-D-psicofuranoside
• CAS: 1242059-04-6
• 化学式: C₅₄H₅₄O₁₃
• 分子量: 911.015
• InChiKey: IIXIJKWBXYUECB-IUFUNRKVSA-N

物化性质

• 沸点：
  951.4±65.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  67.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  157.67
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,6-di-O-benzoyl-β-D-psicofuranoside 在 甲醇 、 sodium tetrahydroborate 、 草酰氯 、 二正丁基氧化锡 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 1,4,6-tri-O-benzoyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Galacto- and Mannosucroses

  摘要：

  A concise synthesis of beta-D-fructofuranosyl alpha-D-galactopyranoside (2), and beta-D-fructofuranosyl alpha-D-mannopyranoside (3) is described. Inversion of the C-3 alpha-hydroxy group of alpha-D-galactopyranosyl and alpha-D-mannopyranosyl beta-D-psicofuranosides 10 and 11 via oxidation and stereoselective reduction furnished the corresponding beta-D-fructofuranosides in excellent yields.

  DOI：

  10.3987/com-10-11974
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,6-di-Obenzoyl-3,4-O-isopropylidene-β-D-psicofuranoside 在 对甲苯磺酸一水合物 作用下， 以 甲醇 为溶剂， 反应 45.0h， 以61%的产率得到2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,6-di-O-benzoyl-β-D-psicofuranoside
  参考文献：
  名称：

  Chemical synthesis of β-d-psicofuranosyl disaccharides

  摘要：

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.030