benzyl 2-deoxy-2-<(2,2,2-trichloroethoxycarbonyl)amino>-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside | 114827-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-2-<(2,2,2-trichloroethoxycarbonyl)amino>-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
• 英文别名: benzyl 2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] 2,2,2-trichloroethyl carbonate
• CAS: 114827-03-1；102794-18-3
• 化学式: C₁₉H₂₁Cl₆NO₉
• 分子量: 620.095
• InChiKey: GZGZEGUMWVGNKD-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  132.78
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-2-<(2,2,2-trichloroethoxycarbonyl)amino>-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 氰化汞 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-β-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
  参考文献：
  名称：

  脂质A的生物活性四乙酰基3-脱氧-D-甘露糖-2-辛磺酸（KDO）-（α2 ---- 6）-D-葡糖胺类似物的合成。

  摘要：

  描述了一种新颖的四乙酰基KDO-(α2→6)-单糖类脂质A的合成方法。同时也提供了它们生物活性的初步分析。

  DOI：

  10.1248/cpb.34.2302
• 作为产物：
  描述：

  benzyl 2-deoxy-4,6-O-isopropylene-2-<(2,2,2-trichloroethoxycarbonyl)amino>-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.25h， 以99%的产率得到benzyl 2-deoxy-2-<(2,2,2-trichloroethoxycarbonyl)amino>-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
  参考文献：
  名称：

  脂质A和相关化合物。十五 高效合成新型的氨基葡萄糖-4-磷酸酯类似物，脂质A的非还原糖部分。

  摘要：

  本文描述了一种有效合成脂质A非还原糖部分的单糖类似物的方法。同时也简要分析了它们的生物活性。

  DOI：

  10.1248/cpb.35.4517

文献信息

• Synthesis of cyclopropyl glycosides and their use as novel glycosyl donors
  作者：Clark Scholl、Thomas Licisyn、Christopher Cummings、Kevin Hughes、David Johnson、Walter Boyko、Robert Giuliano

  DOI：10.1016/j.carres.2012.03.008

  日期：2012.7

  Methods for the synthesis of cyclopropyl glycosides and their use as glycosyl donors are described. Cyclopropyl glycosides containing different substituents were prepared by cyclopropanation of the corresponding vinyl glycosides, or by glycosidation of cyclopropyl alcohols that are synthesized by the Kulinkovich reaction. 1-Methyl- and 1-phenyl-substituted cyclopropyl glycosides undergo coupling to

  描述了合成环丙基糖苷的方法及其用作糖基供体的方法。通过相应的乙烯基糖苷的环丙烷化，或通过由库林科维奇反应合成的环丙基醇的糖苷化，可以制备含有不同取代基的环丙基糖苷。1-甲基和1-苯基取代的环丙基糖苷在TMS三氟甲磺酸酯存在下与Fmoc保护的丝氨酸和苏氨酸以及部分保护的单糖偶联，得到糖基化产物。
• Lipid A and Related Compounds. XVI. Synthesis of Biologically Active Tetraacetyl-3-deoxy-D-&lt;I&gt;manno&lt;/I&gt;-2-octulosonic Acid (KDO) - (&amp;alpha;2&amp;rarr;6) -D-Glucosamine-4-phosphates, Novel Analogs of the Nonreducing Sugar Moiety of Lipid A
  作者：SHIN-ICHI NAKAMOTO、KAZUO ACHIWA

  DOI：10.1248/cpb.35.4537

  日期：——

  Synthesis of biologically active tetraacetyl-3-deoxy-D-manno-2-octulosonic acid- (α2→6) -D-glucosamine-4-phosphate analogs of lipid A is described.

  描述了生物活性四乙酰基-3-脱氧-D-甘露糖-2-八烯酸-(α2→6)-D-氨基葡萄糖-4-磷酸的脂质A类似物的合成。
• Efficient synthesis of novel monosaccharide analogs of lipids A.
  作者：Shinichi Nakamoto、Toshio Takahashi、Kiyoshi Ikeda、Kazuo Achiwa

  DOI：10.1248/cpb.33.4098

  日期：——

  The efficient synthesis of the monosaccharide analogs of lipids A bearing two 3-acyloxytetradecanoyl and phosphoryl groups at the C-2, 3 and C-4 positions of the glucosamine skeleton is described. Also a preliminary analysis of their biological activities is presented.

  描述了具有两个3-酰氧基十四酸和磷酸基团在葡萄糖胺骨架的C-2、C-3和C-4位置的脂质A单糖类似物的高效合成。此外，还呈现了对其生物活性的初步分析。
• A new and stereospecific approach to Kdo-containing disaccharides using phenylselenyl triflate
  作者：Kiyoshi Ikeda、Seijiro Akamatsu、Kazuo Achiwa

  DOI：10.1016/0008-6215(89)84116-3

  日期：1989.6

  Les diholosides sont prepares a partir d'aminoglycosides proteges et de didesoxy-2,3 octeno-2 pyranosulose-2 onate de methyle

  Les diholosides sont制备了部分氨基糖苷类产品和二乙氧基-2,3 octeno-2 pyranosulose-2 onate demethyle
• 3-<i>O</i>-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities
  作者：David A. Johnson、David S. Keegan、C. Gregory Sowell、Mark T. Livesay、Craig L. Johnson、Lara M. Taubner、Annalivia Harris、Kent R. Myers、Jennifer D. Thompson、Gary L. Gustafson、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、Yvonne M. Yorgensen、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1021/jm990222b

  日期：1999.11.1

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.