3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose | 121654-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose
• 英文别名: [(1S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2,7-dioxabicyclo[4.1.0]heptan-3-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 121654-00-0
• 化学式: C₂₄H₅₂O₅Si₃
• 分子量: 504.93
• InChiKey: UKQSMOCKDYHOTE-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 四丁基氟化铵 、 sodium hydride 、 对甲苯磺酸 、 三氟乙酸酐 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 222.0h， 生成 thioethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-d-Glucose Scaffold

  摘要：

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.

  DOI：

  10.1021/jo001099v
• 作为产物：
  描述：

  三-O-(叔丁基二甲基甲硅烷基)-D-葡萄烯糖 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 以100%的产率得到3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose
  参考文献：
  名称：

  关于糖基的直接环氧化：应用迭代策略合成 β-连接的寡糖

  摘要：

  合成这些低聚糖 a partir du tri-O-acetyl-3,4,6 glucal et du dimethyl-3,3 dioxiranne

  DOI：

  10.1021/ja00199a028

文献信息

• Isolation and synthesis of β-miroside an antifungal furanone glucoside from Prumnopitys ferruginea
  作者：Stephen D. Lorimer、Simon D. Mawson、Nigel B. Perry、Rex T. Weavers

  DOI：10.1016/0040-4020(95)00352-9

  日期：1995.6

  The bioactivity-directed isolation and structural determination of β-miroside 3-[(β-D-glucopyranosyloxy)-methyl]-2(5H)-furanone} from the New Zealand gymnosperm Prumnopitys ferruginea, is described. Picein 4-(β-D-glucopyranosyloxy)acetophenone} was also isolated. Syntheses of β-miroside, its α-anomer and an isomer with an exocyclic double bond, are described, along with an unusual reaction of an

  描述了从新西兰裸子植物Prumnopitys ferruginea提取的β-紫罗兰苷3-[（β-D-吡喃葡萄糖基氧基）-甲基] -2（5H）-呋喃酮}的生物活性指导的分离和结构测定。还分离出Picein 4-（β-D-吡喃葡萄糖基氧基）苯乙酮}。描述了β-多侧面苷，其α-端基异构体和具有环外双键的异构体的合成，以及环外烷氧基亚烷基内酯与N-溴代琥珀酰亚胺的不寻常反应，得到具有环内双键的产物。β-Miroside具有抗真菌，抗菌和细胞毒活性。
• Biomimetic Synthesis of a Leaf-opening Factor, Potassium Isolespedezate, by Direct Formation of Enol-glycoside
  作者：Takanori Sugimoto、Minoru Ueda

  DOI：10.1246/cl.2004.976

  日期：2004.8

  However, 1 was synthesized via an indirect route because of the difficulty of direct formation of the enol-glycosidic linkage. More efficiency is desired for the preparation of 1 and 2 which are necessary for the synthesis of probe compounds. In this paper, we report the biomimetic synthesis of 1 containing direct formation of an enol-glucosidic linkage. This efficient route makes it possible to prepare

  Potassium isolespedezate (1) 是一种控制豆科植物夜间叶片运动的叶片张开因子。我们使用根据 1 及其半乳糖类似物的结构设计的合成探针对 nyctinasty 进行了生物有机研究 (2)。然而，1 是通过间接途径合成的，因为直接形成烯醇 - 糖苷键很困难。需要更高的效率来制备合成探针化合物所必需的 1 和 2。在本文中，我们报告了 1 的仿生合成，其中包含直接形成烯醇 - 糖苷键。这种高效的路线使大量制备 1 和 2 成为可能。
• Synthesis and Conformational Analysis of 2-<i>O</i>-Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides
  作者：Ajaz Ahmed、Faheem Rasool、Gurpreet Singh、Meenu Katoch、Debaraj Mukherjee

  DOI：10.1002/ejoc.202000650

  日期：2020.8.2

  Silyl protected nucleosides possess better biological activity. 2‐O‐silylated nucleosides were synthesized by trans opening of 1,2‐anhydrosugar with nucleobases where HMDS acts both as activating, and silylating agent. Conformational analysis and biofilm inhibition activity of synthesized nucleosides were performed.

  甲硅烷基保护的核苷具有更好的生物活性。2- O-甲硅烷基化的核苷是通过将1,2-脱水糖与核苷反式合成的，其中HMDS既是活化剂，又是甲硅烷基化剂。进行了构象分析和生物膜抑制活性的合成核苷。
• Reaction of thiophenol with glucal epoxides: X-ray structure of 3,4,6-tri-O-tert-butyldimethylsilyl-1-S-phenyl-1-thio-α-D-glucopyranoside
  作者：Caroline Walford、Sarah L. Heath

  DOI：10.1039/a704534d

  日期：——

  The reaction of the tert-butyldimethylsilyl protected glucal epoxide 1 with thiophenol under a variety of conditions gives three distinct adducts, including the α-phenylthioglycoside 2a, which exists both in solution and in the solid state in a 1C4 conformation in which the C-2, C-3, C-4 and C-5 substituents are all axial.

  叔丁基二甲基硅烷保护葡聚糖环氧化物1在各种条件下与噻吩酚的反应会产生三种不同的加合物，包括α-苯基硫代糖苷2a，该加合物在溶液和固体状态下都以1C4构象存在，其中C-2、C-3、C-4和C-5取代基均为轴向。
• α-<i>C</i>-Glycosides <i>via</i> <i>syn</i> Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/<i>n</i>-Dibutyl Ether
  作者：Simon Wagschal、Johan Guilbaud、Pauline Rabet、Vittorio Farina、Sébastien Lemaire

  DOI：10.1021/acs.joc.5b01472

  日期：2015.9.18

  The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 degrees C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different Omicron-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the alpha-anomer of canagliflozin.