2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose | 925673-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose
• 英文别名: 2-Amino-2-deoxy-1,3,4,6-tetra-o-(trimethylsilyl)-alpha-d-glucopyranose；(2R,3R,4R,5R,6R)-2,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-3-amine
• CAS: 925673-04-7
• 化学式: C₁₈H₄₅NO₅Si₄
• 分子量: 467.901
• InChiKey: IZQZMEFDJBXMIT-DUQPFJRNSA-N

物化性质

• 沸点：
  402.2±45.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 在 吡啶 、 phosphonothioyl chloride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2-amino-2-deoxy-D-glucopyranose 6-thiophosphate
  参考文献：
  名称：

  WO2008/76156

  摘要：

  公开号：
• 作为产物：
  描述：

  N,O-双三甲硅基乙酰胺 、 2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 作用下， 生成 2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose
  参考文献：
  名称：

  Glucose-Functionalized, Serum-Stable Polymeric Micelles from the Combination of Anionic and RAFT Polymerizations

  摘要：

  Poly(ethylene-alt-propylene)-poly[(N,N-dimethylacrylamide)-grad-(2-methacrylamido glucopyranose)] (PEP-poly(DMA-grad-MAG), or PG) diblock terpolymers were synthesized by combining anionic and reversible addition-fragmentation chain transfer (RAFT) polymerizations. An omega-trithiocarbonate-functionalized PEP homopolymer served as the macromolecular chain transfer agent (macroCTA), and RAFT copolymerizations of DMA and a trimethylsilyl-protected MAG (TMS-MAG) monomer gave a family of PG diblock terpolymers after hydrolysis. The terpolymers had similar degrees of polymerization, and the MAG content ranged from 3.5 to 39 mol % in the hydrophilic block. At 70 degrees C, the reactivity ratios of DMA (1) and TMS-MAG (2) were determined to be r(1) = 1.86 +/- 0.07 and r(2) = 0.16 +/- 0.01, and thus the poly(meth)acrylamide blocks in the PG diblock terpolymers were likely to be gradient copolymers. Micellar dispersions from PG diblock polymers in water were examined by cryogenic transmission electron microscopy (cryo-TEM) and dynamic light scattering (DLS). Spherical micelles with core radii of ca. 7 nm and overall hydrodynamic radii of ca. 15 nm were the predominant morphologies observed in all samples prepared by sequential nanoprecipitation and dialysis. The electron-dense MAG moieties greatly increased the native contrast of the micellar coronae, which were clearly viewed as gray halos around the micellar cores in samples with relatively large MAG content. The stability of the glucose-installed micelles was tested in four biologically relevant media, from simple phosphate-buffered saline (PBS) to fetal bovine serum (FBS), using a combination of DLS and cryo-TEM measurements. Micellar dispersions from a PG diblock terpolymer with 16 mol % of MAG of the hydrophilic block were stable in 100% FBS over at least 14 h, suggesting their minimal interactions with serum proteins. Control experiments suggested that micelles composed of PDMA alone in the corona had similar serum stabilities. These sugar-functionalized micelles hold promise as in vivo drug delivery vehicles to possibly prolong circulation time after intravenous administration.

  DOI：

  10.1021/ma300218n
• 作为试剂：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 、 六甲基二硅氮烷 、 三甲基氯硅烷 在 2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 、 正己烷 、 水 、 盐酸 、 magnesium sulfate 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose
  参考文献：
  名称：

  GLMS RIBOSWITCHES, STRUCTURE-BASED COMPOUND DESIGN WITH GLMS RIBOSWITCHES, AND METHODS AND COMPOSITIONS FOR USE OF AND WITH GLMS RIBOSWITCHES

  摘要：

  glmS核酸开关是抗生素和其他小分子治疗的靶点。化合物可以用于刺激、激活、抑制和/或失活glmS核酸开关。glmS核酸开关的原子结构可用于设计新的化合物，以刺激、激活、抑制和/或失活核酸开关。

  公开号：

  US20100324123A1

文献信息

• New phosphine-imine and phosphine-amine ligands derived from d -gluco-, d -galacto- and d -allosamine in Pd-catalysed asymmetric allylic alkylation
  作者：Izabela Szulc、Robert Kołodziuk、Anna Zawisza

  DOI：10.1016/j.tet.2018.02.009

  日期：2018.3

  New phosphine-imine and phosphine-amine chiral ligands which were easily prepared from d-gluco-, d-galacto- and d-allosamine furnished a high level of enantiomeric excess (up to 99%) in the Pd(0)-catalysed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with malonates.

  容易从d-葡萄糖-，d-半乳糖和d- allosamine制备的新的膦-亚胺和膦-胺手性配体在Pd（0）催化的不对称中提供了高水平的对映体过量（最高达99％）。外消旋的1，3-二苯基-2-丙烯基乙酸酯与丙二酸酯的烯丙基烷基化。
• Selective Acetylation of Non-anomeric Groups of per-<i>O</i>-Trimethylsilylated Sugars
  作者：Welday Desta Weldu、Cheng-Chung Wang

  DOI：10.1021/acs.joc.0c02813

  日期：2021.4.2

  Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact

  糖的羟基的选择性修饰由于其近乎相对的反应性而一直是一个长期的挑战。本文中，我们报道了TMSOTf催化的几种过O -TMS保护的糖底物的非异头羟基的选择性乙酰化，同时不影响其异头基团。除了本身具有通用性之外，可以将完整的异头O -TMS基团官能化，以提供关键的糖前体，如亚氨酸酯供体，否则可以通过逐步的异头脱保护-官能化程序进行合成。
• glucoBox ligand—a new carbohydrate-based bis(oxazoline) ligand. Synthesis and first application
  作者：Mustafa Irmak、Annika Groschner、Mike M. K. Boysen

  DOI：10.1039/b612986b

  日期：——

  The synthesis of a new bis(oxazoline) ligand from D-glucosamine and its application in enantioselective copper(I) catalysed cyclopropanations of olefins is described.

  描述了由D-葡萄糖胺合成新的双（恶唑啉）配体及其在对映选择性铜（I）催化的烯烃环丙烷化中的应用。
• Chemoselective per-O-trimethylsilylation and homogeneous N-functionalisation of amino sugars
  作者：A. Abragam Joseph、Vijay M. Dhurandhare、Chun-Wei Chang、Ved Prakash Verma、Girija Prasad Mishra、Chiao-Chu Ku、Chun-Cheng Lin、Cheng-Chung Wang

  DOI：10.1039/c4cc06645f

  日期：——

  HomogeneousN-functionalisation of amino sugars can be achievedviaefficient CH₃CN-promoted hexamethyldisilazane per-O-trimethylsilylation.

  氨基糖的均相N-官能化可以通过高效的CH3CN促进的六甲基二硅氮烷经过O-三甲基硅基化实现。
• Sweets for Catalysis - Facile Optimisation of Carbohydrate-Based Bis(oxazoline) Ligands
  作者：Tobias Minuth、Mustafa Irmak、Annika Groschner、Tobias Lehnert、Mike M. K. Boysen

  DOI：10.1002/ejoc.200801035

  日期：2009.3

  A new type of carbohydrate-based bis(oxazoline) ligands was prepared from inexpensive D-glucosamine and tested in asymmetric cyclopropanation reactions. For optimisation, modified ligands with 3-O substituents of varying size and electronic properties were prepared as well as a 3-OH unprotected and a perpivaloylated derivative. All new ligands were tested in asymmetric cyclopropanation, revealing a

  一种新型的基于碳水化合物的双（恶唑啉）配体由廉价的 D-葡糖胺制备，并在不对称环丙烷化反应中进行了测试。为了优化，制备了具有不同大小和电子特性的 3-O 取代基的修饰配体以及未保护的 3-OH 和全新戊酰化衍生物。所有新配体都在不对称环丙烷化中进行了测试，揭示了对映选择性对 3-O 残基的空间需求和电子特性的强烈依赖性。此外，观察到由环状缩醛基团的存在或不存在决定的吡喃糖构象的显着影响。因此，很容易将新的碳水化合物双（恶唑啉）配体调整到给定的反应。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）