2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate | 188913-44-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate
• 英文别名: [(2S,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 188913-44-2
• 化学式: C₁₆H₂₀Cl₃NO₁₀
• 分子量: 492.695
• InChiKey: IBUZGVQIKARDAF-HPCHECBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate 在 氢氧化钾 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Sphingolipids and Glycerolipids. IV. Syntheses and Ionophoretic Activities of Several Analogues of Soya-cerebroside II, a Calcium Ionophoretic Sphingoglycolipid Isolated from Soybean.

  摘要：

  为了研究结构-活性关系，我们利用先前报道的鞘糖脂合成方法，合成了大豆神经酰胺II（2）的五种类似物[（2'R）-2'-羟基棕榈酰（3）、棕榈酰（4）、（2'S）-2'-羟基棕榈酰（5）、β-D-半乳糖基（6）和8, 9-二氢（7）相关物]，2是从大豆中分离出的钙离子载体鞘氨醇糖脂。通过使用W-08（液膜型）装置和人体红细胞膜方法的检测表明，（2'R）-2'-羟基棕榈酰类似物（3）对钙离子的离子结合和离子渗透活性高于以3为主要成分的大豆神经酰胺II（2）。还发现其他类似物（5, 6, 7, 8）没有那些离子载体活性。合成了（2'R）-2'-羟基棕榈酰类似物（3）的对映体（8），并检测了其钙离子载体活性。化合物8显示出与3相等的钙离子结合活性，但8缺乏支持钙离子通过人体红细胞膜的能力。因此，人体红细胞膜在钙离子载体活性方面精确区分了3和8的绝对构型。

  DOI：

  10.1248/cpb.41.1534
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide 在 potassium carbonate 、 silver carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 48.5h， 生成 2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: the first enantiomer of a natural acetal glucoside

  摘要：

  The synthesis of (2S)-2-beta-L-glucopyranosyloxy-4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, the enantiomer of the natural acetal glucoside GDIMBOA from maize, has been achieved by the double diastereoselective L-glucosylation of racemic 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one with 2,3,4,6-tetra-O-acetyl-beta-L-glucopyranosyl trichloroacetimidate in the presence of excess of boron trifluoride etherate as promoter as well as protecting and equilibrating agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00303-5

文献信息

• Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives
  作者：Blandine Clique、Alan Ironmonger、Benjamin Whittaker、Jacqueline Colley、James Titchmarsh、Peter Stockley、Adam Nelson

  DOI：10.1039/b505865a

  日期：——

  A library of forty modified aminoglycosides was prepared in which the configuration and regiochemistry of two or three rings was widely varied. The library was based around three core ring systems: the 2-deoxystreptamine ring system found in the natural products, and both enantiomers of (1R*,2R*,4R*,5R*)-2,5-diamino-cyclohexane-1,4-diol and (1R*,3R*,4R*,6R*)-4,6-diaminocyclohexane-1,3-diol. In each

  制备了四十个修饰的氨基糖苷文库，其中两个或三个环的构型和区域化学变化很大。该文库基于三个核心环系统：天然产物中存在的2-脱氧链胺胺环系统，以及（1R *，2R *，4R *，5R *）-2,5-二氨基-环己烷-1， 4-二醇和（1R *，3R *，4R *，6R *）-4,6-二氨基环己烷-1,3-二醇。在每种情况下，通过一个或两个糖环的糖基化修饰核心。糖取代基的绝对构型（d或l），端基异构中心（α或β）以及胺的区域化学排列均发生了变化。
• Synthesis, structural revision, and tyrosinase inhibitory activity of proposed phloretin-4-O-β-D-glucopyranoside from <i>Homalium stenophyllum</i>
  作者：Ryo Shimakage、Ken-ichi Nihei

  DOI：10.1080/14786419.2020.1817922

  日期：2022.4.3

  Phloretin-4-O-beta-D-glucopyranoside (1), isolated fromHomalium stenophyllum, was synthesized for the first time through aldol condensation and Schmidt glycosylation reactions aiming to develop a novel hydrophilic tyrosinase inhibitor. However, the specific rotation of synthetic1was found to be negative and different from that reported for natural product1. Thus, L-glucoside2was chemically synthesized using the established synthetic route of1, suggesting that the configuration of the natural product1was the same as that of2, as their specific rotation and spectroscopic data were also the same. In addition, the evaluation of the inhibitory activity of1and2against tyrosinase indicated that2was 1.4 times more potent than1, but they were both relatively weak. Therefore, the enantiomeric analogues1and2were proved to be unique tyrosinase inhibitors due to the chiral recognition from the tyrosinase active site.
• The Synthesis of <scp>l</scp>-Aminosugar and the Studies of <scp>l</scp>-Pyranoses on the Ring III of Pyranmycins
  作者：Jinhua Wang、Jie Li、David Tuttle、Jon Y. Takemoto、Cheng-Wei Tom Chang

  DOI：10.1021/ol026588r

  日期：2002.11.1

  [GRAPHICS]The synthesis of a novel class of aminoglycoside, pyranmycin, and a convenient method for the preparation of 6-amino-L-idopyranosides were reported. One of the members in the reported pyranmycin families, TC010, has prominent activity against Escherichia coli, Staphylococcus aureus, and Bacillus megaterium. We also discovered that the C-4(1) chair conformation on ring III of pyranmycin is essential for the antibacterial activity.
• Double diastereoselection explains limitations in synthesizing mannose-containing β-(1,3)-glucans
  作者：Balla Sylla、Karine Descroix、Christophe Pain、Cédric Gervaise、Frank Jamois、Jean-Claude Yvin、Laurent Legentil、Caroline Nugier-Chauvin、Richard Daniellou、Vincent Ferrières

  DOI：10.1016/j.carres.2010.04.018

  日期：2010.7

  It is known that 3-O-glycosylation of glucosidic acceptors bearing acyl groups in the 4 and 6 positions instead of a 4,6-O-benzylidene ring mainly affords a-glycosides. Described here is an unexpected stereochemical outcome for elongation at glucose O-3 of a beta-D-Glcp-(1 -> 3)-alpha-D-Manp disaccharide using peracetylated ethyl thioglucoside as a donor. This unexpected reaction was correlated with match-mismatch effects, as shown by efficient coupling of the same acceptor by a donor of L-configuration. (C) 2010 Elsevier Ltd. All rights reserved.