1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-7-enitol | 856668-29-6

• 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: 1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-7-enitol
• 英文别名: 1-propenyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranose
• CAS: 856668-29-6
• 化学式: C₁₇H₂₄O₉
• 分子量: 372.372
• InChiKey: HRYHAUJVZHFTNE-UHDSXZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-7-enitol 在 咪唑 、 potassium osmate(VI) 、 sodium periodate 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of C6′′-modified α-C-GalCer analogues as mouse and human iNKT cell agonists

  摘要：

  合成并评估了将已知的Th1极化C6''-修饰与C-糖苷键结合的α-GalCer类似物作为iNKT细胞抗原。

  DOI：

  10.1039/c7ob00081b
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium dichloride 氢溴酸 、 六正丁基二锡 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 71.0h， 生成 1,3,4,5-tetra-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-7-enitol
  参考文献：
  名称：

  C-Linked Galactosyl Serine AFGP Analogues as Potent Recrystallization Inhibitors

  摘要：

  A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.

  DOI：

  10.1021/ol050677x

文献信息

• Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
  申请人：Tsuji Moriya

  公开号：US20050222048A1

  公开（公告）日：2005-10-06

  The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R 3 is OH or a monosaccharide and R 4 is hydrogen, or R 3 is hydrogen and R 4 is OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.

  该发明涉及以下化合物的新颖化合物：其中X为O或NH；R3为OH或单糖，R4为氢，或R3为氢，R4为OH或单糖；R5为氢或单糖；以及其药用盐或酯。该发明还涉及这些化合物的直接使用以及作为免疫佐剂用于治疗癌症、传染病和自身免疫疾病。该发明还涉及合成这些中间体的方法，这些中间体可用于制备这些新颖化合物。
• Intramolecular Hydrogen Abstraction Reaction Promoted by Alkoxy Radicals in Carbohydrates. Synthesis of Chiral 2,7-Dioxabicyclo[2.2.1]heptane and 6,8-Dioxabicyclo[3.2.1]octane Ring Systems
  作者：Cosme G. Francisco、Antonio J. Herrera、Ernesto Suárez

  DOI：10.1021/jo026004z

  日期：2002.10.1

  for the synthesis of chiral 6,8-dioxabicyclo[3.2.1]octane and 2,7-dioxabicyclo[2.2.1]heptane ring systems under neutral conditions. This reaction can be considered to be an intramolecular glycosidation that goes through an intramolecular hydrogen abstraction promoted by an alkoxy radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology is useful

  特定保护的脱水醛糖醇与（二乙酰氧基碘）苯或碘基苯与碘的反应是合成手性6,8-二氧杂双环[3.2.1]辛烷和2,7-二氧杂双环[2.2.1]庚烷环的温和选择性步骤系统在中性条件下。该反应可被认为是分子内糖苷化，其经历由烷氧基自由基促进的分子内氢提取，然后将瞬时的C-自由基中间体氧化成氧碳鎓离子。该方法不仅可用于手性合成子的制备，而且可用于碳水化合物骨架的特定碳的选择性氧化，这是合成被保护的果糖的良好方法。
• Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis
  作者：Guangwu Chen、John Schmieg、Moriya Tsuji、Richard W. Franck

  DOI：10.1021/ol0482137

  日期：2004.10.1

  Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.