allyl 2-O-benzyl-3,4-O-isopropylidene-α-D-xylopyranoside | 196859-36-6

• 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: allyl 2-O-benzyl-3,4-O-isopropylidene-α-D-xylopyranoside
• 英文别名: allyl 2-O-benzyl-3,4-di-O-isopropylidene-α-D-xylopyranoside；(3aR,6S,7R,7aS)-2,2-dimethyl-7-phenylmethoxy-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 196859-36-6
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: VRGUBWLCFRSMPS-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 2-O-benzyl-3,4-O-isopropylidene-α-D-xylopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以3.87 g的产率得到allyl 2-O-benzyl-α-D-xylopyranoside
  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 吡啶 、 sodium hydroxide 、 sodium hydride 、 对甲苯磺酸 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 allyl 2-O-benzyl-3,4-O-isopropylidene-α-D-xylopyranoside
  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

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：——
• 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.