2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,4,6-tri-O-benzoyl-β-D-psicofuranoside | 1245770-67-5

• 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 1,4,6-tri-O-benzoyl-β-D-psicofuranoside
• 英文别名: [(2R,3S,4R,5S)-3-benzoyloxy-5-(benzoyloxymethyl)-4-hydroxy-5-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 1245770-67-5
• 化学式: C₆₁H₅₈O₁₄
• 分子量: 1015.12
• InChiKey: QQQYDCMDYSHWKA-KUXDFIIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  75
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,4,6-tri-O-benzoyl-β-D-psicofuranoside 在 甲醇 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 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-O-benzoyl-β-D-psicofuranoside 、 苯甲酰氯 在 二正丁基氧化锡 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.92h， 以74%的产率得到2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl 1,4,6-tri-O-benzoyl-β-D-psicofuranoside
  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

文献信息

• Synthesis of Galacto- and Mannosucroses
  作者：Jun'ichi Uenishi、Atsushi Ueda、Takanori Yamashita

  DOI：10.3987/com-10-11974

  日期：——

  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.