6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate | 129210-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
• 英文别名: [(1R,2R,3S,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydroxycyclohexyl] dihydrogen phosphate
• CAS: 129210-15-7
• 化学式: C₁₂H₂₄NO₁₃P
• 分子量: 421.295
• InChiKey: LOPKUYZFWDPPJT-LFIKJOHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  253
• 氢给体数：
  10
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 以20%的产率得到(3aS,4R,5S,6S,7R,7aR)-2,5,6,7-四羟基-2-氧代六氢-1,3,2-苯并二氧磷杂戊环-4-基 2-氨基-2-脱氧-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  1D-4-O-和1D-6-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-肌醇1-磷酸酯和1D-6的合成和可能的胰岛素样活性研究-O-（2-氨基-2-脱氧-α-D-吡喃葡萄糖基）-肌醇1，2-（环状磷酸酯）。

  摘要：

  从先前合成的中间体开始，报道了糖基-肌醇1-磷酸酯1和2以及糖基-肌醇1，2-（环状磷酸酯）3的合成。发现化合物3对雏鸡胚胎的早期发育的内耳显示出增殖作用。

  DOI：

  10.1016/0008-6215(94)00178-2
• 作为产物：
  描述：

  2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-D-myo-inositol 在 palladium on activated charcoal 、 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 氨 、 水 、 氢气 、 碘 、 TMSOTf 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 90.58h， 生成 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
  参考文献：
  名称：

  An Effective Strategy for the Synthesis of 6-O-(2-Amino-2-deoxy-.alpha.-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-Phosphate Related to Putative Insulin Mimetics

  摘要：

  Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

  DOI：

  10.1021/jo00090a035

文献信息

• Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors
  作者：Per J. Garegg、Peter Konradsson、Stefan Oscarson、Katinka Ruda

  DOI：10.1016/s0040-4020(97)10238-1

  日期：1997.12

  2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides

  合成6- ø - （2-氨基-2-脱氧- α-d-D-吡喃葡萄糖基）-D-肌醇-1-磷酸，内芯结构中的各种glycosylphosphatidylinositols找到，并且相应的1,2-环磷酸酯，描述了作为胰岛素第二信使糖基肌醇磷酸酯的一部分提出的方法。分子的肌醇部分中的手性是通过使用已知的D-樟脑缩醛中间体来实现的。糖基化使用4 - O-烯丙基-2-叠氮基3，6-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖基氟作为糖基供体。烯丙基可以被化学选择性地去除，从而打开了一条与葡糖胺单元的4位结合的寡糖的途径。磷酸化通过氨基磷酸酯方法完成。
• Cottaz, Sylvain; Brimacombe, John S.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1673 - 1678
  作者：Cottaz, Sylvain、Brimacombe, John S.、Ferguson, Michael A. J.

  DOI：——

  日期：——
• Synthesis of the Core Tetrasaccharide of <i>Trypanosoma </i><i>c</i><i>ruzi</i> Glycoinositolphospholipids: Man<i>p</i>(α1→6)-Man<i>p</i>(α1→4)-6-(2-aminoethylphosphonic acid)-GlcN<i>p</i>(α1→6)-<i>m</i><i>yo</i>-Ins-1-PO₄
  作者：Markus Hederos、Peter Konradsson

  DOI：10.1021/jo0508595

  日期：2005.9.1

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.
• Synthesis and characterization of an insulin-mimetic disaccharide
  作者：Robert Plourde、Marc D'Alarcao、Alan R. Saltiel

  DOI：10.1021/jo00035a015

  日期：1992.4

  A glucosaminyl-inositol-1,2-cyclic phosphate, 1, has been synthesized and evaluated for selected insulin-mimetic properties. The compound was designed to resemble structurally the recently reported inositol glycans which are believed to be insulin second messengers. The synthesis utilized a Koenigs-Knorr glycosylation of optically pure 1-camphanyl-2,3:4,5-di-O-cyclohexylidene-D-myo-inositol with 2-azido-3,4,6-tri-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide followed by phosphitylation by the phosphoramidite method, oxidation, and carbodiimide cyclization. Compound 1 was found to stimulate lipogenesis in rat adipocytes in a dose-dependent manner in the micromolar range up to a level 30-40% of that maximally induced by insulin.