2,5-di-O-methyl-myo-inositol | 137037-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-di-O-methyl-myo-inositol
• CAS: 137037-84-4
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: DYQWYDODKPTUPA-FLMNKLAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.53
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,5-di-O-methyl-myo-inositol 在 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 2,5-di-O-methyl-1,3,4,6-tetrakis(diethoxyphospho)-myo-inositol
  参考文献：
  名称：

  Synthesis of potent Ins(1,4,5)P3 5-phosphatase inhibitors by modification of myo-inositol 1,3,4,6-tetrakisphosphate

  摘要：

  Three myo-inositol tetrakisphosphate analogues were synthesised based upon myo-inositol 1,3,4,6-tetrakisphosphate: 2,5-di-O-methyl myo-inositol-1,3,4,6-tetrakisphosphate 19 and its phosphorothioate derivative 22, together with myo-inositol 1,3,4,6 tetrakisphosphorothioate 25. These compounds were prepared by phosphitylating 2,5-di-0-methyl-myo-inositol and 2,5-di-O-benzyl-myo-inositol followed by oxidation with t-butylhydroperoxide or sulfoxidation at room temperature using sulfur in a mixed solvent of DMF and pyridine. Sulfoxidation was complete within 15 min; however, without DMF, the reaction was much slower, and required overnight. When evaluated against Ins(1,4,5)P-3 5-phosphatase, 3-kinase and for Ca2+ release at the Ins(1,4,5)P3 receptor, only weak activity was observed for Ca2+ release. 22 and 25 are potent 5-phosphatase inhibitors and 25 is a moderate inhibitor of 3-kinase. Thus, we have synthesised potent enzyme inhibitors, which do not mobilise Ca2+ and devised conditions for quick, clean and inexpensive sulfoxidation of inositol polyphosphite intermediates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00347-x
• 作为产物：
  描述：

  (1S,2R,3R,4R,5S,6R)-2,5-Bis-benzyloxy-3,6-dimethoxy-cyclohexane-1,4-diol 生成 2,5-di-O-methyl-myo-inositol
  参考文献：
  名称：

  The preparation of intermediates for the synthesis of 1d-myo-inositol 1,4,5-trisphosphate, a second messenger for signal transduction in cells

  摘要：

  Racemic 1,2,4-tri-O-benzyl-5,6-0-isopropylidene-myo-inositol was prepared by a new route involving crotyl (but-2-enyl) ethers and converted into the (-)-omega-camphanates to give the pure crystalline 1L-diastereoisomer and the chirally impure, syrupy ID-diastereoisomer. The latter was converted via the 1-0-allyl or 1-0-p-methoxybenzyl ethers into chirally pure ID-2,3,6-tri-O-benzyl-myo-inositol [required as an intermediate for the synthesis of ID-myo-inositol 1,4,5-trisphosphate (1,4,5-IP3)], which was also prepared by de-p-methoxybenzylation of ID-2,3,6-tri-O-benzyl-1,5-di-0-p-methoxybenzyl-myo-inositol. Racemic 2,4-di-O-benzyl-5,6-0-isopropylidene-1-0-p-methoxybenzyl-myo-inositol was prepared in a similar way to the analogous tribenzyl ether (using crotyl ethers) and the omega-camphanate esters behaved similarly, allowing efficient resolution by crystallisation of the (-)- and (+)-omega-camphanates. Racemic 1,2,4-tri-O-allyl-3-0-(but-2-enyl)-myo-inositol was resolved via the (-)-omega-camphanates and was also converted into 1,2,4-tri-O-(CiS-prop-1-enyl)-myo-inositol, an alternative intermediate for the synthesis of 1,4,5-IP3.

  DOI：

  10.1016/0008-6215(92)85035-x

文献信息

• Tetrakisphosphates and Bispyrophosphates of myo-Inositol Derivatives as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Oxygen Release
  作者：Alexandros E. Koumbis、Carolina D. Duarte、Claude Nicolau、Jean-Marie Lehn

  DOI：10.1002/cmdc.201000421

  日期：2011.1.3

  of these proved to be efficient allosteric effectors, with similar affinities for hemoglobin to that of myo‐inositol hexakisphosphate, which is one of the best known allosteric effectors of hemoglobin. The efficacy was found to be higher for free phosphates than pyrophosphates. As allosteric Hb effectors, these compounds enable enhanced oxygen release. These effects increase with the strength of Hb

  各种2,5-和1,4-取代的和未取代的肌醇肌醇tetrakisphosphates和制备bispyrophosphates进行以下的一般合成途径。测试了所有最终化合物诱导氧气从人血红蛋白释放的能力。其中大多数被证明是有效的变构效应子，对血红蛋白的亲和力与对肌红蛋白的亲和力相似肌醇六磷酸酯，是最著名的血红蛋白变构效应物之一。发现游离磷酸盐的功效比焦磷酸盐更高。作为变构Hb效应物，这些化合物可增强氧气释放。这些效应随着Hb结合强度的增加而增加，并且主要对应于静电相互作用。立体化学和位阻因素在分子识别中也起着重要但次要的作用。鉴于缺氧在多种类型的疾病发挥了中心作用，勘探肌肌醇磷酸衍生物的代表在寻求作用于组织的氧合状态，并可能在发现和开发潜力显著物质的重要途径新型药物候选者。
• The allylation of dibutylstannylene derivatives of myo -inositol
  作者：Trupti Desai、Jill Gigg、Roy Gigg、Sheila Payne、Soledad Penades、Henry J. Rogers

  DOI：10.1016/0008-6215(92)84162-l

  日期：1992.9

  O -allyl- myo -inositol (from myo -inositol). Parallel results were obtained when crotyl bromide was used. When 3 equiv. of dibutyltin oxide were used with myo -inositol or 1 equiv. with the mixture of di- O -allyl derivatives, 1,3,4-tri- O -allyl- myo -inositol was the major product. When 2 equiv. of dibutyltin oxide were used, myo -inositol gave a complex mixture of mono-, di-, and tri- O -allyl derivatives

  摘要在四丁基溴化铵存在下，肌醇或外消旋的1,4-，1,6-和4,5-二-O-烯丙基-肌醇在乙腈中的反应与二丁基氧化锡和烯丙基溴的反应作为主要产品，易分离的1,3,4,6-和1,3,4,5-四-O-烯丙基-肌醇的混合物与少量的五-O-烯丙基-肌醇的混合物肌醇和1,3,5-三-O-烯丙基-肌醇（来自肌醇）。当使用巴豆基溴化物时，获得了平行的结果。当3个当量。将二丁基氧化锡与肌醇或1当量一起使用。与二-O-烯丙基衍生物的混合物一起使用的主要产品是1,3,4-三-O-烯丙基-肌醇。当2当量。使用二丁基氧化锡，肌醇产生单，双，以及三-O-烯丙基衍生物，其在转化为O-异亚丙基衍生物之后被分馏。外消旋的1,3,4,5-四-O-烯丙基-肌醇通过（-）-ω-樟脑酸酯拆分。
• Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring <i>myo</i> ‐inositol with 1,4‐cyclohexanedione
  作者：Atsushi Sudo、Tomoki Yamasaki、Takuro Yamashita、Dai Ishida

  DOI：10.1002/pola.29461

  日期：2019.12.15

  Oligo(spiroketal)s (OSKs) were synthesized from myo‐inositol, a naturally occurring cyclic compound bearing six hydroxyl groups. The successful synthesis of OSKs was achieved using silyl ethers 2 derived from 1,4‐di‐O‐alkylated myo‐inositol 1 as monomers, which underwent polycondensation with 1,4‐cyclohexanedione (CHD) at 0 °C in the presence of trimethylsilyl triflate as a catalyst. Because of the

  寡（螺酮）（OSK）是由肌醇合成的，肌醇是一种天然存在的带有六个羟基的环状化合物。OSKs成功合成用甲硅烷基的醚获得2衍生自1,4-二ö烷基化肌醇肌醇1作为单体，其后行缩聚与三甲基甲硅烷的存在下1,4-环己二酮（CHD）在0℃下三氟甲磺酸酯为催化剂。由于甲硅烷基醚与酮的缩合反应具有不可逆的性质，因此所得的OSK 7的分子量比以前报道的通过四醇1的缩聚反应获得的OSK更高。CHD时，缩酮功能发生向后水解。此外，另一系列OSKs，的8，使用甲硅烷基醚合成3由2,5-二-衍生ö烷基化肌醇肌醇6，这是更对称的单体不是硅烷基醚2。甲硅烷基醚3与CHD进行了有效的缩聚反应，而四醇6没有进行缩聚反应，这表明将此类四醇衍生为相应的甲硅烷基醚是获得OSK的有效策略。©2019 Wiley Periodicals，Inc.J.Polym。科学，A部分：Polym。化学 2019，57，2407年至2414年
• WO2008/82658
  申请人：——

  公开号：——

  公开（公告）日：——
• MYO-INOSITOL TRISPYROPHOSPHATE AS AN ANTI-OBESITY AGENT
  申请人：NormOxys, Inc.

  公开号：EP2968617A1

  公开（公告）日：2016-01-20