α-1,5-anhydro-1-C-(2-trimethylsilylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol | 141100-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-1,5-anhydro-1-C-(2-trimethylsilylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol
• 英文别名: trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane；trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]silane
• CAS: 141100-79-0
• 化学式: C₃₉H₄₄O₅Si
• 分子量: 620.861
• InChiKey: XOXSQZSZQDXZOO-GFRPZHATSA-N

物化性质

• 沸点：
  677.4±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-1,5-anhydro-1-C-(2-trimethylsilylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol 在 4-二甲氨基吡啶 、 sodium hydroxide 、 正丁基锂 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 α-1,5-anhydro-1-C-(2-trimethylsilylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m

文献信息

• [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：VERTEX PHARMA

  公开号：WO2014100158A1

  公开（公告）日：2014-06-26

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物具有化学式（I）。该发明还提供含有这些化合物的药学上可接受的组合物，以及使用这些组合物治疗细菌感染的方法。最后，该发明提供了制备本发明化合物的方法。
• Direct <i>C</i>-Glycosylation of Organotrifluoroborates with Glycosyl Fluorides and Its Application to the Total Synthesis of (+)-Varitriol
  作者：Jing Zeng、Seenuvasan Vedachalam、Shaohua Xiang、Xue-Wei Liu

  DOI：10.1021/ol102473k

  日期：2011.1.7

  C-glycosides via BF3·Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

  据报道，通过BF 3 ·Et 2 O促进了有机三氟硼酸酯和糖基氟化物的偶联，采用了温和，立体选择性和快速的方法访问炔基和烯基C-糖苷。该方法的应用通过仅七个步骤的简明有效的全合成（+）-varitriol进一步得到了证明。
• Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues
  作者：Toshio Nishikawa、Yuya Koide、Shigeo Kajii、Kyoko Wada、Miyuki Ishikawa、Minoru Isobe

  DOI：10.1039/b414905j

  日期：——

  The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.

  通过 10 个步骤（包括以下关键步骤：甘露糖衍生物与链烷乙炔的 C-糖苷化反应、卡斯特罗吲哚合成、Sc(ClO4)3 促进与 L-丝氨酸衍生的氮丙啶羧酸酯偶联）从市售的δ-甲基-D-甘露糖苷中完全合成了δ-C-甘露糖基色氨酸（C-Man-Trp），这是一种天然的 C-糖基氨基酸。C-Man-Trp 的葡萄糖和半乳糖类似物也是用类似方法合成的。本文简要讨论了合成的 C-糖基色氨酸及其合成中间体的构象分析。
• MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20140243283A1

  公开（公告）日：2014-08-28

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物的化学式为I：本发明还提供包含该化合物的药学上可接受的组合物，并提供使用该组合物治疗细菌感染的方法。最后，本发明提供了制备该化合物的方法。
• Mannose Derivatives for Treating Bacterial Infections
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20160235775A1

  公开（公告）日：2016-08-18

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula I: The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

  本发明涉及用于治疗或预防细菌感染的化合物。这些化合物的化学式为I：本发明还提供了含有这些化合物的药学上可接受的组合物以及使用这些组合物治疗细菌感染的方法。最后，本发明还提供了制备本发明化合物的方法。