1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose | 352286-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose
• CAS: 352286-01-2
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: ZOZFJPZWPQUPRD-XMEMRUQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose 在 palladium on activated charcoal 四氮唑 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.67h， 生成 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] β-D-xylopyranoside 3,4,3'-trisphosphate
  参考文献：
  名称：

  Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity

  摘要：

  The synthesis of a series of tetrahydrofuranyl alpha- and beta -xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha -D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3 'S,4 'R)-3-hydroxytetrahydrofuran-4-yl] alpha -D-xylopyranoside 3,4,3 ' -trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P-3; a beta -linked analogue, 1-O-[(3 'R,4 'S)-3-hydroxytetrahydrofuran-4-yl] beta -D-xylopranoside 3,4,3 ' -trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P-3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue. (C) 2001 Elsevier Science I,td. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00067-2
• 作为产物：
  描述：

  2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranose 在 四氮唑 、 silver perchlorate 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.66h， 生成 1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-β-D-xylopyranose
  参考文献：
  名称：

  Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity

  摘要：

  The synthesis of a series of tetrahydrofuranyl alpha- and beta -xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha -D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3 'S,4 'R)-3-hydroxytetrahydrofuran-4-yl] alpha -D-xylopyranoside 3,4,3 ' -trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P-3; a beta -linked analogue, 1-O-[(3 'R,4 'S)-3-hydroxytetrahydrofuran-4-yl] beta -D-xylopranoside 3,4,3 ' -trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P-3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue. (C) 2001 Elsevier Science I,td. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00067-2