(1S,2S,3R,4S,5R,6R)-2-Hydroxymethyl-4,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,3,5-triol | 166320-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,3R,4S,5R,6R)-2-Hydroxymethyl-4,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,3,5-triol
• CAS: 166320-97-4
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: ZLNBTGPKTYNPOP-YVMUJHKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  117.84
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4S,5R,6R)-2-Hydroxymethyl-4,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,3,5-triol 在 四氮唑 、 盐酸 、 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 Phosphorous acid dibenzyl ester (1R,2S,3S,4R,5R,6S)-2,6-bis-benzyloxy-3-benzyloxymethyl-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester
  参考文献：
  名称：

  6-Deoxy-6-hydroxymethyl scyllo-inositol 1,2,4-trisphosphate: A potent agonist at the inositol 1,4,5-trisphosphate receptor

  摘要：

  The synthesis of racemic 6-deoxy-6-hydroxymethyl scyllo-inositol 1,2,4-trisphosphate is described. This compound is a highly potent agonist at the platelet D-myo-inositol 1,4,5-trisphosphate receptor, and it binds to the rat cerebellar receptor with an affinity equal to that of the natural ligand. These results suggest that the 5 ''-hydroxymethyl group of adenophostin A may contribute to its unusual potency. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00399-x
• 作为产物：
  描述：

  (1S,3S,5S,7R,8S,9R)-8,9-Bis-(4-methoxy-benzyloxy)-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one 在 盐酸 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 (1S,2S,3R,4S,5R,6R)-2-Hydroxymethyl-4,6-bis-(4-methoxy-benzyloxy)-cyclohexane-1,3,5-triol
  参考文献：
  名称：

  A Conformationally Restricted Cyclic Phosphate Analogue of Inositol Trisphosphate:  Synthesis and Physicochemical Properties

  摘要：

  The design and total synthesis of DL-6-deoxy-6-(hydroxymethyl)-scyllo-inositol 1:7-cyclic 2,4-trisphosphate (4), a conformationally restricted cyclic phosphate analogue of the second messenger inositol 1,4,5-trisphosphate [Ins(1,4,5)P(3)], is described. The protected inosose 2,4,6/3,5-pentahydroxy-3,5-bis-O-(p-methoxybenzyl)-2,4,6-O-methylidynecyclohexanone (7) was obtained from myoinositol orthoformate in two steps, and Wittig methylenation and then hydroboration-oxidation using 9-BBN-H/OH(-)/H(2)O(2) gave the axial hydroxymethyl derivative 9. A series of protection/ deprotection steps provided the diol 13, which was converted into two cyclic phosphate esters 14a and 14b, epimeric at phosphorus, by reaction with (benzyloxy)bis(N,N-diisopropylamino)phosphine /1H-tetrazole followed by m-CPBA. Two other hydroxyl groups were then exposed and phosphorylated, and total deprotection gave racemic 4. NMR studies confirmed that in 4 the phosphate group equivalent to the 4-phosphate of Ins(1,4,5)P(3) is held in the positive gauche orientation and that the inositol ring maintains a chair conformation from pH 2 to 12. Investigation of the acid-base properties of 4 using potentiometric and (31)P NMR techniques showed that, over the physiological pH range, 4 behaves as a diprotic acid and that the ionization of the phosphate group equivalent to the 5-phosphate of Ins(1,4,5)P(3) is enhanced. In biological assays, 4 appears to behave as a weak full agonist at the platelet Ins(1,4,5)P(3) receptor, and the possible interpretation of this result is discussed.

  DOI：

  10.1021/jo9714425

文献信息

• Synthesis of a Conformationally Restricted Cyclic Phosphate Analog of Inositol Triphosphate
  作者：Andrew M. Riley、Barry V. L. Potter

  DOI：10.1021/jo00121a006

  日期：1995.8