(3aS,4R,6S,7aS)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one | 922520-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aS,4R,6S,7aS)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS: 922520-75-0
• 化学式: C₂₇H₄₆O₁₃
• 分子量: 578.654
• InChiKey: YBLCLTBRVYQBBG-FMRZRFRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6S,7aS)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-one 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 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
  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

文献信息

• Improved Preparation of β‐<scp>d</scp>‐ManNAc‐(1→4)‐<scp>d</scp>‐Glc and β‐<scp>d</scp>‐TalNAc‐(1→4)‐<scp>d</scp>‐Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR‐P1 and CD69 Receptors
  作者：Emanuele Attolino、Filippo Bonaccorsi、Giorgio Catelani、Felicia D'Andrea、Karel Křenek、Karel Bezouška、Vladimir Křen

  DOI：10.1080/07328300802030845

  日期：2008.6

  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.