4-O-[2-deoxy-3,4-O-isopropylidene-2-oximino-β-D-lyxo-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 1044747-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-[2-deoxy-3,4-O-isopropylidene-2-oximino-β-D-lyxo-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS: 1044747-29-6
• 化学式: C₂₃H₃₉NO₁₂
• 分子量: 521.562
• InChiKey: WXNITERELGEFGK-QHJYBFDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  145.12
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-O-[2-deoxy-3,4-O-isopropylidene-2-oximino-β-D-lyxo-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Improved Preparation of β‐d‐ManNAc‐(1→4)‐d‐Glc and β‐d‐TalNAc‐(1→4)‐d‐Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR‐P1 and CD69 Receptors

  摘要：

  The synthetic access of either beta-D-ManNAc-(1-->4)-D-Glc (5) is beta-d-TalNAc-(1-->4)-D-Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79-91 and 2004, 23, 179-190), optimizing the preparation of suitably protected 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-beta-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2'-oximino precursors derived from lactose. The affinity of the disaccharides 5 and 6 toward the natural killer cell NKR-P1 and CD69 receptors has been evaluated and discussed.

  DOI：

  10.1080/07328300802030845
• 作为产物：
  描述：

  4-O-[2-deoxy-3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-2-oximino-β-D-lyxo-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以96%的产率得到4-O-[2-deoxy-3,4-O-isopropylidene-2-oximino-β-D-lyxo-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Improved Preparation of β‐d‐ManNAc‐(1→4)‐d‐Glc and β‐d‐TalNAc‐(1→4)‐d‐Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR‐P1 and CD69 Receptors

  摘要：

  The synthetic access of either beta-D-ManNAc-(1-->4)-D-Glc (5) is beta-d-TalNAc-(1-->4)-D-Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79-91 and 2004, 23, 179-190), optimizing the preparation of suitably protected 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-beta-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2'-oximino precursors derived from lactose. The affinity of the disaccharides 5 and 6 toward the natural killer cell NKR-P1 and CD69 receptors has been evaluated and discussed.

  DOI：

  10.1080/07328300802030845