1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside | 145416-95-1

• 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: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-β-D-galactopyranose；1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl)amido-β-D-galactopyranose；1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranose；1,3,4,6-tetra-O-acetyl-2-N-(2,2,2-trichloroethoxycarbonyl)-β-D-galactosamine；[(2R,3R,4R,5R,6S)-3,4,6-triacetyloxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 145416-95-1
• 化学式: C₁₇H₂₂Cl₃NO₁₁
• 分子量: 522.721
• InChiKey: LREZJCUWSKPMMD-UXXRCYHCSA-N

物化性质

• 沸点：
  562.2±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.33h， 生成 6-chlorohexyl (3,4,6-tri-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient Synthesis of 3,6-Dideoxy-β-d-arabino-hexopyranosyl-Terminated LacdiNac Glycan Chains of the Trichinella spiralis Parasite

  摘要：

  The synthesis of a linear trisaccharide epitope of the Trichinella spiralis N-linked glycan, in a form amenable to glycoconjugate formation, is reported. The trisaccharide contains the synthetically challenging LacdiNAc [beta-GalpNAc(1-->4)-beta-GlcpNAc] element, as well as a terminal 3,6-dideoxy-beta-D-arabino-hexopyranose (tyvelose) residue. An orthogonal protection strategy is described, which permits the protection and manipulation of three amino groups present in the disaccharide beta-GalNAc(1-->4)-beta-GlcNAc and the tether used to prepare neoglycoconjugates. The beta-linked dideoxyhexose was generated in excellent yield by the introduction of the dideoxyhexose unit as a beta-D-ribo-hexopyranoside (paratose) followed by an oxidation-reduction sequence to generate the beta-D-arabino configuration in high diastereomeric excess. The required dideoxyhexose donor was synthesized in a series of high-yielding steps from glucose utilizing the p-methoxyphenyl glycoside.

  DOI：

  10.1021/jo991812k
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 吡啶 、 4-二甲氨基吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.0h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of N‐Protected Galactosamine Building Blocks from d‐Tagatose via the Heyns Rearrangement

  摘要：

  N -Acetyl-d-galactosamine (11), a very important naturally occurring building block of oligosaccharides, is easily accessible via the Heyns rearrangement of (D)-tagatose (3) with benzylamine. The short and efficient synthesis of various differently N -protected (D)-galactosamine derivatives is reported.

  DOI：

  10.1080/07328300500495795

文献信息

• Convenient stereocontrolled amidoglycosylation of alcohols with acetylated glycals and trichloroethoxysulfonamide
  作者：Teiichi Murakami、Yukari Sato、Kyoko Yoshioka、Mutsuo Tanaka

  DOI：10.1016/j.carres.2016.09.001

  日期：2016.11

  of alcohols has been developed using O-acetylated glycals, trichloroethoxysulfonamide, and iodosobenzene. This one-pot amidoglycosylation was applied to a variety of primary and secondary alcohols to afford the beta-O-glycosides with acceptable yields up to 84%. The reaction would proceed via stereoselective intermolecular aziridination of the glycal from the alpha-face followed by SN2 reaction with

  使用O-乙酰基化的糖，三氯乙氧基磺酰胺和碘代苯，已经开发出了区域和立体控制的铑（II）催化的醇酰胺糖基化反应。将这种一锅式酰胺基糖基化反应应用于各种伯醇和仲醇，以高达84％的可接受收率得到β-O-糖苷。该反应将通过α面的糖的立体选择性分子间叠氮化进行，然后与β面的C-1处的醇进行SN2反应，仅得到1,2：2,3-二-反式取代的异构体。
• Saccharide Fluorescent Substrates, Preparation Method and Uses Thereof
  申请人：Texier-Nogues Isabelle

  公开号：US20080299044A1

  公开（公告）日：2008-12-04

  The invention concerns saccharide type fluorescent enzymatic substrates comprising on the same saccharide unit a fluorophor F1 and an inhibitor of the fluorescence of F1, and their use for preparing a diagnostic reagent for in vivo functional imaging, as well as a diagnostic reagent containing at least such an enzymatic substrate.

  这项发明涉及糖类荧光酶底物，其在同一糖类单元上包含荧光色团F1和F1荧光抑制剂，并且它们用于制备用于体内功能成像的诊断试剂，以及含有至少这种酶底物的诊断试剂。
• ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis
  作者：Peng Peng、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1016/j.carres.2013.11.009

  日期：2014.1

  glycosyl building blocks. These thioglycosides prevented the aglycon transfer and enhanced the efficiency of glycosyl coupling reactions, especially in the reactions of disarmed donors with armed acceptors. Moreover, these thioglycosides were employed in preactivation-based one-pot oligosaccharide assembly.

  硫糖苷广泛用于正交糖基化，武装解除武装的化学选择性糖基化和基于预激活的糖基化。然而，在硫糖苷的糖基化过程中偶尔发生糖苷配基转移。在基于预激活的反应中也遇到了这个问题，这在一定程度上限制了基于预激活的糖基化的应用。为了解决这个问题，引入了空间受阻的糖苷配基邻甲基苯基硫代糖苷作为糖基结构单元。这些硫糖苷可防止糖苷配基转移并提高糖基偶联反应的效率，特别是在解除武装的供体与武装受体的反应中。而且，这些硫代糖苷被用于基于预活化的一锅寡糖组装中。
• High-Yielding Catalytic Synthesis of Glycosyl Azides from Peracylated Sugars
  作者：Koki Matsubara、Teruaki Mukaiyama

  DOI：10.1246/cl.1994.247

  日期：1994.2

  In the presence of a catalyst generated from SnCl4 and AgClO4, or Yb(OTf)3 various glycosyl azides are synthesized in high yields with complete stereoselectivities from peracylated sugars and trimethylsilyl azide by choosing a suitable solvent such as dichloromethane or nitromethane.

  在由 SnCl4 和 AgClO4 或 Yb(OTf)3 生成的催化剂存在下，通过选择合适的溶剂，例如二氯甲烷或硝基甲烷，可以从过酰化糖和三甲基甲硅烷基叠氮化物以高产率合成各种糖基叠氮化物，具有完全立体选择性。
• Glycosylation with N-Troc-protected glycosyl donors
  作者：Ulf Ellervik、Göran Magnusson

  DOI：10.1016/0008-6215(95)00318-5

  日期：1996.1

  N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-be

  将N-Troc保护的（Troc = 2,2,2-三氯乙氧基羰基）葡萄糖胺和半乳糖胺糖基供体（1-O-乙酰基糖，溴糖和硫代糖苷）与相应的N-Phth保护的衍生物的糖基化为2 -（三甲基甲硅烷基）乙醇，2-溴乙醇，3-巯基丙酸甲酯，N-Fmoc保护的丝氨酸和2-（三甲基甲硅烷基）乙基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖苷。N-Troc保护的供体比N-Phth保护的供体以更高的收率得到纯的β-糖苷。N-Troc保护基可通过用锌还原来去除，从而允许在同时包含N-Troc和N-Phth基团的寡糖中进行选择性N-脱保护。