allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside | 196859-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside
• 英文别名: allyl 2-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-xylopyranoside；(2S,3R,4S,5R)-4,5-bis[(4-methoxyphenyl)methoxy]-3-phenylmethoxy-2-prop-2-enoxyoxane
• CAS: 196859-37-7
• 化学式: C₃₁H₃₆O₇
• 分子量: 520.623
• InChiKey: DKEIOOMRPZMLCP-ITGKQZKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside 在 palladium dichloride 四氮唑 、 silver perchlorate 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.66h， 生成 1-O-[(3'R,4SR)-3-hydroxytetrahydrofuran-4-yl] 2-O-benzyl-α-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
• 作为产物：
  描述：

  D-吡喃木糖 在 camphor-10-sulfonic acid 、 水 、 sodium hydride 、 乙酰氯 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.58h， 生成 allyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-xylopyranoside
  参考文献：
  名称：

  Jenkins, David J.; Potter, Barry V. L., Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 41 - 50

  摘要：

  DOI：

文献信息

• Moitessier, Nicolas; Maigret, Bernard; Chretien, Francoise, European Journal of Organic Chemistry, 2000, # 6, p. 995 - 1005
  作者：Moitessier, Nicolas、Maigret, Bernard、Chretien, Francoise、Chapleur, Yves

  DOI：——

  日期：——
• Jenkins, David J.; Potter, Barry V. L., Journal of the Chemical Society. Perkin transactions I, 1998, # 1, p. 41 - 50
  作者：Jenkins, David J.、Potter, Barry V. L.

  DOI：——

  日期：——
• Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity
  作者：Heidi J. Rosenberg、Andrew M. Riley、Rachel D. Marwood、Vanessa Correa、Colin W. Taylor、Barry V.L. Potter

  DOI：10.1016/s0008-6215(01)00067-2

  日期：2001.5

  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.