(1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 1092961-90-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: [(3aR,4S,6R,6aR)-4-(benzoyloxymethyl)-2,2-dimethyl-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]methyl benzoate
• CAS: 1092961-90-4
• 化学式: C₅₇H₅₈O₁₃
• 分子量: 951.08
• InChiKey: YDJVPJKQHMDJLN-YQBWFPAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  70
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 45.0h， 生成 (1,6-di-O-benzoyl-β-D-psicofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  2,3,4,6-四-o-苄基-D-吡喃葡萄糖 、 (1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranosyl) benzyl phthalate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以58%的产率得到(1,6-di-O-benzoyl-3,4-O-isopropylidene-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.
• Chemical synthesis of β-d-psicofuranosyl disaccharides
  作者：Atsushi Ueda、Takanori Yamashita、Jun’ichi Uenishi

  DOI：10.1016/j.carres.2010.05.030

  日期：2010.8

  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.