methyl 4-O-(1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 1242058-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-(1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS: 1242058-99-6
• 化学式: C₅₁H₅₄O₁₃
• 分子量: 874.982
• InChiKey: ZFIFWSSKAVWVIW-CBQYGQSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  64.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  135.67
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 (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 2.0h， 以57%的产率得到methyl 4-O-(1,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-psicofuranosyl)-2,3,6-tri-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