(2S,3R,4S,5R,6R)-2-Allyloxy-3-benzyloxy-6-benzyloxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran | 181777-23-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-Allyloxy-3-benzyloxy-6-benzyloxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran
• CAS: 181777-23-1
• 化学式: C₃₉H₄₄O₈
• 分子量: 640.774
• InChiKey: RTIDQIYJFBGDGC-QGVRFUEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  47.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.84
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-Allyloxy-3-benzyloxy-6-benzyloxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran 在 吡啶 、 甲醇 、 草酰氯 、 二甲基亚砜 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol
  参考文献：
  名称：

  C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

  摘要：

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00175-0
• 作为产物：
  描述：

  allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (2S,3R,4S,5R,6R)-2-Allyloxy-3-benzyloxy-6-benzyloxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  C-Glycoside based mimics of d-myo-inositol 1,4,5-trisphosphate

  摘要：

  Epimeric C-glycoside based polyphosphates, alpha- and beta-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside, was prepared in five steps (67% yield) from allyl alpha-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P-3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P-3 receptor ligands. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00175-0

文献信息

• A Ca2+-mobilising carbohydrate-based polyphosphate: synthesis of 2-hydroxyethyl α-d-glucopyranoside 2′,3,4-trisphosphate
  作者：David J. Jenkins、Barry V.L. Potter

  DOI：10.1016/0008-6215(96)00078-x

  日期：1996.6

  Two routes to a glucose-based mimic of the second messenger 1D-myo-inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 alpha: beta-anomeric mixture of allyl glucopyranosides (5ab) from which the pure alpha anomer 5a was isolated by crystallisation. Treatment of 5ab with

  描述了两种与腺苷A相关的第二信使1D-肌醇1,4,5-三磷酸基于葡萄糖的模拟途径。在强阳离子交换树脂的存在下，用烯丙醇对D-葡萄糖进行费歇尔糖基化反应，得到烯丙基葡萄糖吡喃糖苷（5ab）的7：3α：β-异头物混合物，通过结晶从中分离出纯净的α异头物5a。用1.05当量的二丁基氧化锡，然后用2.1当量的苯甲酰氯处理5ab，得到烯丙基2,6-二-O-苯甲酰基-α-D-吡喃葡萄糖苷，将其分三步转化为烯丙基2,6-二-O-苄基-3,4-O-异亚丙基-α-D-吡喃葡萄糖苷（4）。或者，用2.5当量的二丁基氧化锡，然后用苄基溴处理5a，得到烯丙基2，6-二-O-苄基-α-D-吡喃葡萄糖苷（9），该烯丙基也转化为4。在方便的一锅反应中，将化合物4修饰为磷酸化前体2-羟乙基2,6-二-O-苄基-α-D-吡喃葡萄糖苷（12），然后将12磷酸化并解封，得到2-羟乙基α- D-吡喃葡萄糖苷2'，3,4-三磷酸。2
• Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of 1,4,5-trisphosphate
  作者：Rachel D. Marwood、Andrew M. Riley、Vanessa Correa、Colin W. Taylor、Barry V.L. Potter

  DOI：10.1016/s0960-894x(99)00006-2

  日期：1999.2

  The synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-alpha-D-glucopyranoside 3,4,3'-trisphosphate (7), a novel Ca2+ mobilising agonist at the Ins(1,4,5)P-3 receptor, designed by excision of two motifs of adenophostin A is reported, defining a potential minimal structure for potent glucopyranoside-based agonists of Ins(1,4,5)P-3 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.