(1,4,6-tri-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 1092961-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,4,6-tri-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5S)-3-benzoyloxy-5-(benzoyloxymethyl)-4-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl benzoate
• CAS: 1092961-93-7
• 化学式: C₆₁H₅₈O₁₄
• 分子量: 1015.12
• InChiKey: QQQYDCMDYSHWKA-PLWOGUNKSA-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：

  (1,4,6-tri-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(1,4,6-tri-O-benzoyl-β-D-erythro-2,3-hexodiulofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (+)-sucrose via β-d-psicofuranosylation

  摘要：

  Despite the difficulty of direct beta-furanosylation with D-fructose, the synthesis of beta-D-fructofuranosyl alpha-D-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via beta-selective D-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. D-Psicofuranosyl donor 10 was prepared in eight steps from D-ribose monoacetomide 3 in excellent yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.008
• 作为产物：
  描述：

  (1,6-di-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 、 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59%的产率得到(1,4,6-tri-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of (+)-sucrose via β-d-psicofuranosylation

  摘要：

  Despite the difficulty of direct beta-furanosylation with D-fructose, the synthesis of beta-D-fructofuranosyl alpha-D-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via beta-selective D-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. D-Psicofuranosyl donor 10 was prepared in eight steps from D-ribose monoacetomide 3 in excellent yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.008

文献信息

• Synthesis of (+)-sucrose via β-d-psicofuranosylation
  作者：Jun’ichi Uenishi、Atsushi Ueda

  DOI：10.1016/j.tetasy.2008.09.008

  日期：2008.9

  Despite the difficulty of direct beta-furanosylation with D-fructose, the synthesis of beta-D-fructofuranosyl alpha-D-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via beta-selective D-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. D-Psicofuranosyl donor 10 was prepared in eight steps from D-ribose monoacetomide 3 in excellent yield. (C) 2008 Elsevier Ltd. All rights reserved.