5-hydroxy-3-oxa-pentyl 3,6-di-O-acetyl-2-acetamido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranoside | 247226-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-3-oxa-pentyl 3,6-di-O-acetyl-2-acetamido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranoside
• CAS: 247226-05-7
• 化学式: C₃₀H₄₅NO₁₉
• 分子量: 723.683
• InChiKey: FGXRKIJSOPEXOS-QSBAJRGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  50.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  253.28
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-oxa-pentyl 3,6-di-O-acetyl-2-acetamido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到5-hydroxy-3-oxa-pentyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Studies on carbohydrates. Part 33: Synthesis of spacer-armed 2-acetamido-2-deoxy-4-O-β-d-galactopyranosyl-α-d-mannosides and their dimers

  摘要：

  The mixture of 3,6-di-O-acetyl-4-0-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-azido-2-deoxy-Dpyranosyl 1-acetates or 1-trichloroacetates and the corresponding mannose type glycosyl donors reacted with the spacer arms di- and triethylene glycol, in dichloromethane solution with BF3. OEt2 and TMSOTf as promoters at room temperature to give highly selective products. Only the mannose type products were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00277-3
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-((2R,3S,4S)-4-acetoxy-2-acetoxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester 在 sodium azide 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 溶剂黄146 作用下， 反应 24.0h， 生成 5-hydroxy-3-oxa-pentyl 3,6-di-O-acetyl-2-acetamido-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Studies on carbohydrates. Part 33: Synthesis of spacer-armed 2-acetamido-2-deoxy-4-O-β-d-galactopyranosyl-α-d-mannosides and their dimers

  摘要：

  The mixture of 3,6-di-O-acetyl-4-0-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-azido-2-deoxy-Dpyranosyl 1-acetates or 1-trichloroacetates and the corresponding mannose type glycosyl donors reacted with the spacer arms di- and triethylene glycol, in dichloromethane solution with BF3. OEt2 and TMSOTf as promoters at room temperature to give highly selective products. Only the mannose type products were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00277-3