(1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) benzyl phthalate | 1092961-88-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) benzyl phthalate
• 英文别名: 2-O-[(3aR,4S,6R,6aR)-4,6-bis(benzoyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl] 1-O-benzyl benzene-1,2-dicarboxylate
• CAS: 1092961-88-0
• 化学式: C₃₈H₃₄O₁₁
• 分子量: 666.681
• InChiKey: NMHFHRBEAUHHQA-QDLRKLKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranose 、 邻苯二甲酸单苄酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) benzyl phthalate 、 (1,6-di-O-benzoyl-3,4-O-isopropylidene-α-D-psicofuranosyl) benzyl phthalate
  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.