L-camphor dimethyl acetal | 128525-51-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: L-camphor dimethyl acetal
• 英文别名: (1S,4S)-2,2-dimethoxy-1,7,7-trimethylbicyclo[2.2.1]heptane
• CAS: 128525-51-9
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: RRCYFCPKYNYACP-ONGXEEELSA-N

物化性质

• 沸点：
  213.7±13.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-camphor dimethyl acetal 在 盐酸 、 4 A molecular sieve 、 硫酸 、 sodium hydride 、 sodium cyanoborohydride 、 N,N-二异丙基乙胺 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 69.0h， 生成 (2R,3S,4R,5R,6R)-6-[(1'S,2R,3aS,4R,4'S,5S,6S,7R,7aR)-1',7',7'-trimethyl-5,6,7-tris(phenylmethoxy)spiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,2'-bicyclo[2.2.1]heptane]-4-yl]oxy-5-azido-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-ol
  参考文献：
  名称：

  Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

  摘要：

  Short synthetic routes to protected derivatives of 2-amino-2-deoxy-alpha-D-glucopyranosyl-(1-->6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting front, D-Glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3-D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01241-8
• 作为产物：
  描述：

  左旋樟脑 、 原甲酸三甲酯 在 硫酸 作用下， 以 甲醇 为溶剂， 以495 mg的产率得到L-camphor dimethyl acetal
  参考文献：
  名称：

  通过缩醛形成去对称化合成加勒比雪卡毒素 C-CTX-1 的 MN 环

  摘要：

  加勒比雪卡毒素 C-CTX-1 的 MN 环是由对应于 M 环的内消旋顺式-2,7-二甲基氧杂环庚烷衍生物通过与樟脑衍生物形成缩醛的去对称作用合成的，然后通过 Horner 构建 N 环–Wadsworth-Emmons 反应和缩醛形成。通过在流动条件下共轭外型二烯的光诱导电环化合成内消旋-顺式-2,7-二甲基氧杂环庚烷衍生物，得到环丁烯衍生物，然后通过氧化裂解和β-羟基酮的非对映选择性还原进行扩环。

  DOI：

  10.1021/acs.orglett.3c04013

文献信息

• Inositol-phosphate derivatives and method of detecting inositol-1-phosphate
  申请人：CIS Bio International

  公开号：US08178704B2

  公开（公告）日：2012-05-15

  The present invention relates to inositol phosphate derivatives, in which the inositol phosphate is substituted with one or two reactive groups G or one or two conjugated substances or molecules M, said reactive group(s) G or said substance(s) or molecule(s) M being linked to IP1 via a linkage group L, M being chosen from the following group: a tracer, an immunogen, a member of a binding partner pair, a solid support. Application: tools allowing the study of the inositol phosphate cycle and therefore, indirectly, the study of seven transmembrane domain receptors coupled to phospholipase C, receptors having a tyrosine kinase activity, and in general enzymes involved in the variations of the intracellular concentration of IP1.

  本发明涉及肌醇磷酸衍生物，其中肌醇磷酸被一个或两个反应基团G或一个或两个共轭物质或分子M取代，所述反应基团G或所述物质或分子M通过连接基团L与IP1相连，M选择自以下组：示踪剂、免疫原、结合伙伴对的成员、固体支持。应用：工具，允许研究肌醇磷酸循环，因此间接地研究与磷脂酶C偶联的七膜跨膜结构受体、具有酪氨酸激酶活性的受体，以及一般参与细胞内IP1浓度变化的酶。
• Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
  作者：Stuart J. Conway、James Gardiner、Simon J. A. Grove、Melloney K. Johns、Ze-Yi Lim、Gavin F. Painter、Diane E. J. E. Robinson、Christine Schieber、Jan W. Thuring、Leon S.-M. Wong、Meng-Xin Yin、Antony W. Burgess、Bruno Catimel、Phillip T. Hawkins、Nicholas T. Ktistakis、Leonard R. Stephens、Andrew B. Holmes

  DOI：10.1039/b913399b

  日期：——

  The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A–E is described. These core compounds were obtained from myo-inositol orthoformate 1via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution–protection process using camphor acetals 10. Coupling of cores A–E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins.

  报道了从五个关键的核心中间体A-E合成完整的磷脂酰肌醇磷酸类似物（PIPs）家族的方法。这些核心化合物通过选择性DIBAL-H和三甲基铝介导的裂解以及使用樟脑乙缩醛的解析保护过程，从肌醇原甲酸1中获得。将核心A-E与从所需保护的脂质侧链衍生的磷酰胺34和38偶联，得到了完全保护的PIPs。通过使用钯黑或碳上的钯氢氧化物在碳酸氢钠存在下的氢解，去除了剩余的保护基团，得到了完整的二棕榈酰和氨基PIP类似物42、45、50、51、58、59、67、68、76、77、82、83、92、93、99和100。利用包含这些化合物的亲和探针进行的研究，鉴定了参与PI3K细胞内信号网络的新蛋白，并允许对磷脂酰肌醇相互作用蛋白进行全面的蛋白质组学分析。
• [EN] CAMPHANYLIDENE AND PHENYLALKYL INOSITOL POLYPHOSPHATE COMPOUNDS, COMPOSITIONS, AND METHODS OF THEIR USE<br/>[FR] COMPOSES DE CAMPHANYLIDENE ET POLYPHOSPHATES D'INOSITOL PHENYLALKYLE, COMPOSITIONS ET LEURS PROCEDES D'UTILISATION
  申请人：INOLOGIC INC

  公开号：WO2004087721A1

  公开（公告）日：2004-10-14

  This invention relates to new camphanylidene and phenyl alkyl inositol polyphosphate derivatives that inhibit the absorption of sodium ions in epithelial cells and regulate inducible nitric oxide synthase (iNOS) in macrophages. The invention provides methods for inhibiting sodium ion absorption by epithelial cells and/or regulating inducible nitric oxide synthase (iNOS) in macrophages, by treating epithelial cells or administering to a patient in need of such treatment a therapeutically effective amount of camphanylidene and/or phenyl alkyl inositol polyphosphate compound. Representative camphanylidene and phenyl alkyl inositol polyphosphate compounds include, for example, 1,2-camphanylidene-myo-inositol 3,4,5,6-tetrakisphosphate octakis (propionoxymethyl) ester (INO-4996), 2,3-camphanylidene-myo-inositol 1,4,5,6­-tetrakisphosphate octakis (propionoxymethyl) ester (INO-4984) and 2-O-butyryl-1-O-(3-­phenylpropyl)-myo-inositol 3,4,5,6-tetrakisphosphate octakis (propionoxymethyl) ester (INO-4997).

  这项发明涉及新的松节醇亚烯基和苯基烷基肌醇多磷酸衍生物，能够抑制上皮细胞中钠离子的吸收并调节巨噬细胞中的诱导型一氧化氮合酶（iNOS）。该发明提供了通过治疗上皮细胞或向需要此类治疗的患者施用松节醇亚烯基和/或苯基烷基肌醇多磷酸化合物的治疗方法，以抑制上皮细胞中的钠离子吸收和/或调节巨噬细胞中的诱导型一氧化氮合酶（iNOS）。代表性的松节醇亚烯基和苯基烷基肌醇多磷酸化合物包括，例如，1,2-松节醇亚烯基-肌醇3,4,5,6-四磷酸八(丙酰氧甲基)酯（INO-4996）、2,3-松节醇亚烯基-肌醇1,4,5,6-四磷酸八(丙酰氧甲基)酯（INO-4984）和2-O-丁酰基-1-O-(3-苯基丙基)-肌醇3,4,5,6-四磷酸八(丙酰氧甲基)酯（INO-4997）。
• The synthesis of homochiral inositol phosphates from myo-inositol
  作者：K.Michał Pietrusiewicz、Grzegorz M. Salamończyk、Karol S. Bruzik、Wanda Wieczorek

  DOI：10.1016/s0040-4020(01)88305-8

  日期：1992.1

  conversion of myo-inositol into homochiral inositol phosphates is presented, and is illustrated with total synthesis of myo-inositol 1-phosphate, 2-deoxy-myo-inositol 1-phosphate, myo-inositol 3-phosphate, myo-inositol 4-phosphate, myo-inositol 1,4-bisphosphate, myo-inositol 1,4,5-trisphosphate, and myo-inositol 3,4,5,6-tetrakisphosphate. The syntheses start with selfresolving myo-inositol camphanylidene

  高效转换的一个新的合成方法肌醇肌醇成纯手性肌醇磷酸被呈现，并且与全合成所示肌醇-1-磷酸，2-脱氧肌醇-1-磷酸，肌醇肌醇-3-磷酸，肌肌醇-4-磷酸，肌醇肌醇1,4-二磷酸，肌醇肌醇1,4,5-三磷酸和肌醇肌醇3,4,5,6-四磷酸盐。该合成开始selfresolving肌肌醇camphanylidene顺-monoacetals 2A和2A'分别从母体环糖醇和D-和L-樟脑二甲基缩醛一步获得，并通过沉淀驱动的平衡方便地收获。合成的关键步骤是2a和2a'的选择性单磷酸化，选择性双甲硅烷基化和选择性三酰基化，以及使用二氯磷酸二苄酯和2-二甲氨基-5,6-苯并-1,3,2-二氧杂磷杂环戊烷来实现单磷酸化和多磷酸化。为了支持立体化学分配，还提出了一种中间体完全保护的肌醇衍生物之一的X射线结构。
• SYNTHETIC ANALOGUES OF PHOSPHATIDYL-MYO-INOSITOL MANNOSIDES WITH AN INHIBITORY ACTIVITY OF THE INFLAMMATORY RESPONSE
  申请人：Quesniaux Fyffel Valérie

  公开号：US20110224162A1

  公开（公告）日：2011-09-15

  The present invention relates to novel synthetic analogues of phosphatidyl-myo-inositol mannosides (hereinafter referred to as PIMs) of general formula (I): or a pharmaceutically acceptable salt thereof, to the method for preparing same and to the use thereof in the prevention or treatment of a disease associated with the overexpression of cytokines or of chemokines, in particular of TNF and/or of IL-12. The invention also relates to a pharmaceutical composition comprising at least one synthetic derivative of PIM.

  本发明涉及磷脂酰肌醇甘露聚糖的新型合成类似物（以下简称为PIMs），其一般公式为（I）或其药学上可接受的盐，以及其制备方法和在预防或治疗与细胞因子或趋化因子过表达相关的疾病中的应用，特别是TNF和/或IL-12。该发明还涉及包含至少一种PIM的合成衍生物的药物组合物。