1D-4-O-benzyl-myo-inositol | 68737-75-7

• 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: 1D-4-O-benzyl-myo-inositol
• 英文别名: 1L-4-O-benzyl-myo-inositol；4-O-benzyl-D-myo-inositol；4-O-benzyl-myo-inositol；4-O-Benzyl-sn-myoinositol
• CAS: 68737-75-7
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: RWDNROPIZFGEAU-PJGZEUCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.61
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110.38
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1D-4-O-benzyl-myo-inositol 在 palladium dihydroxide sodium phosphate buffer 、 氢气 、 双氧水 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， -42.0~50.0 ℃ 、310.27 kPa 条件下， 反应 35.0h， 生成 L-1,3,4,5-tetra-O-(methoxymethyl)-myo-inositol 2,6-bis(diethylphosphate)
  参考文献：
  名称：

  Divergent Synthesis of All Possible Optically Active Regioisomers ofMyo‐Inositol Mono‐ and Bisphosphates

  摘要：

  All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups.[GRAPHICS]

  DOI：

  10.1080/07328300701540225
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 2.0h， 生成 1D-4-O-benzyl-myo-inositol
  参考文献：
  名称：

  1d-和1l-4-O-苄基-肌醇，1d-4-O-α-1-呋喃果糖基-肌醇（与天然糖苷相同）和1l-4-O-α-1的合成-fucopyranosyl-肌醇

  摘要：

  摘要从人尿中分离得到的α-1-呋喃核糖基肌醇是该物质与非对映异构体1 l -4- O-肌醇的明确合成，是一维-4-O-肌醇的衍生物。 -肌醇衍生物。通过亚氨酸酯方法，用于糖苷化的手性五-O-苯甲酰基-肌醇，分别由1 d-和1 l -4- O-苄基-肌醇制备。后者解析为相应的外消旋4-O-苄基-1,6：2,3-二-O-环己叉基-肌醇的l（+）-O-乙酰扁桃酸酯。

  DOI：

  10.1016/0008-6215(85)90021-7

文献信息

• Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
  作者：Richard Daniellou、Christopher P. Phenix、Pui Hang Tam、Michael C. Laliberte、David R. J. Palmer

  DOI：10.1039/b417757f

  日期：——

  Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

  来自枯草芽孢杆菌的肌醇脱氢酶（EC 1.1.1.18）显示出在活性位点旁有一个非极性腔，使得保护的消旋肌醇衍生物如4-O-苯甲基-myoinositol能够以非常高的表观立体选择性被识别。
• Achieving molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate through crystal formation
  作者：Richa Sardessai、Shobhana Krishnaswamy、Mysore S. Shashidhar

  DOI：10.1039/c2ce26199e

  日期：——

  Molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate, an early intermediate during the synthesis of phosphoinositols, depends on the phase in which it is stored. This orthoformate is stable when stored in the crystalline form or as solution in common organic solvents. The former has eluded chemists since the preparation of this benzyl ether two decades ago. The difficulty in obtaining crystals of this orthoformate is due to the cleavage of the orthoformate moiety during storage in the gummy state. Dimorphs (form I and form II) of crystalline racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate, were obtained when the gummy sample was stored over extended periods of time. Form I crystals could be obtained consistently, by crystallization of a frozen (−20 °C) solid sample, from a solution of dichloromethane–light petroleum. The two crystal forms display dissimilar patterns of hydrogen bonding and molecular assembly in the solid-state.

  外消旋的4-O-苄基-肌醇-1,3,5-原酸酯在合成磷脂肌醇过程中的早期中间体的分子稳定性取决于其储存的相态。这种原酸酯在结晶形式或以常见有机溶剂的溶液形式储存时稳定。自从二十年前制备了这种苄基醚以来，前者的稳定性一直令化学家们困惑不解。难以获得这种原酸酯的晶体是由于其在胶状储存期间原酸酯部分的断裂。当胶状样品长时间储存后，得到了外消旋的4-O-苄基-肌醇-1,3,5-原酸酯的两种晶态形式（I型和II型）。通过将从二氯甲烷-轻石油溶液中冷冻（−20 °C）的固体样品结晶，可以持续获得I型晶体。这两种晶态形式在固态中的氢键模式和分子组装方式显示出不同的模式。
• Synthesis of some benzyl and methyl ethers of myo-inositol
  作者：Per J. Garegg、Bengt Lindberg、Ingemar Kvarnström、Stefan C.T. Svensson

  DOI：10.1016/s0008-6215(00)90816-4

  日期：1988.3

  Abstract The 1 d and 1 d forms of 1,2,4,5,6- and 1,2,3,4,5-penta- O -methyl- myo -inositol have been prepared from the corresponding chiral mono- O -benzyl derivatives. Convenient preparations are also described of achiral derivatives of 1-, 2-, 4-, and 5- O -benzyl- myo -inositol and of achiral 1,2,4,5,6- and 1,3,4,5,6- myo -inositol by selective benzylation through stannylidene derivatives and through

  摘要从相应的手性单-O-制备了1,2,4,5,6-和1,2,3,4,5-五-O-甲基-肌醇的1 d和1 d形式。苄基衍生物。还描述了1-，2-，4-和5-O-苄基-肌醇的非手性衍生物以及非手性1,2,4,5,6-和1,3,4,5的方便制备方法， 6-肌醇通过亚苄基衍生物的选择性苄基化和亚苄基乙缩醛的还原性裂解而形成。
• Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 2): Via Nonsymmetrical Conduritol B Derivatives
  作者：Michael A. L. Podeschwa、Oliver Plettenburg、Hans-Josef Altenbach

  DOI：10.1002/ejoc.200400918

  日期：2005.7

  myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivatives can be obtained by breaking the C2 symmetry of conduritol B derivatives. A wide variety of myo-inositol phosphates can be synthesized by combining the previously reported symmetrical approach with

  一种实用的路线的制备描述肌醇肌醇磷酸盐。可以通过对乙酰氨基乙酸二硬脂醇关键中间体的酶促拆分，从对苯醌制备两种形式的光学纯化合物。单取代的肌醇衍生物可通过破坏Conduritol B衍生物的C 2对称性而获得。各种各样的肌肌醇磷酸盐可以通过组合与这个新的非对称的方法先前报道的对称方法来合成。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）
• Enhancing Intermolecular Benzoyl-Transfer Reactivity in Crystals by Growing a “Reactive” Metastable Polymorph by Using a Chiral Additive
  作者：Chebrolu Murali、Mysore S. Shashidhar、Rajesh G. Gonnade、Mohan M. Bhadbhade

  DOI：10.1002/chem.200801484

  日期：2009.1

  undergo a clean intermolecular benzoyl‐group‐transfer reaction, form I crystals are less reactive and undergo non‐specific benzoyl‐group transfer leading to a mixture of products. The role played by the additive in fine‐tuning small changes that are required in the molecular packing opens up the possibility of creating new polymorphs that show varied physical and chemical properties. Crystals of D‐2,6‐d

  可以说服通常以单斜晶形式结晶的外消旋2,4-二-O-苯甲酰基-肌醇-1,3,5-原乙酸酯（晶型I，空间群P 2 1 / n）结晶为通过使用少量的D-或L -2,4-二-O-苯甲酰基-肌醇-1,3,5-原甲酸酯作为添加剂添加亚稳态多晶型物（II型，空间群C 2 / c）结晶介质。通过仔细研究先前的外消旋2,4-二-O-苯甲酰基-的结晶结果，选择了结构相似的对映体添加剂。肌醇-1,3,5-原乙酸酯。可以在约145℃下将II型晶体热转变为I型晶体。在这些双晶片的分子的相对组织在分子的螺旋组件，即，亲电致发光（EL）⋅⋅⋅nucleophile（女）和C而言略有不同H⋅⋅⋅π相互作用，但这些微小的变化对两种晶型中的苯甲酰基基团转移反应的便利性和特异性都产生了深远的影响。II型晶体进行清洁的分子间苯甲酰基基团转移反应，而I型晶体的反应性较低，并进行非特异性的苯甲酰基基团转移，从而导致产物混合。添加