trans-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(prop-1'-enyl)-α-D-galactopyranose | 799267-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(prop-1'-enyl)-α-D-galactopyranose
• 英文别名: (2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-[(E)-prop-1-enyl]oxane
• CAS: 799267-93-9
• 化学式: C₃₇H₄₀O₅
• 分子量: 564.722
• InChiKey: JSVYFQPZEROOSG-IGLWWNQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  trans-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(prop-1'-enyl)-α-D-galactopyranose 在 PhCH=Ru[1,3-bis(2,4,6-Me₃C₆H₂)-2-imidazolidinylidene]Cl₂ 三环己基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Efficient Synthesis of α-C-Galactosyl Ceramide Immunostimulants: Use of Ethylene-Promoted Olefin Cross-Metathesis

  摘要：

  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.

  DOI：

  10.1021/ol0482137
• 作为产物：
  描述：

  3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 在 cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以83%的产率得到trans-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(prop-1'-enyl)-α-D-galactopyranose
  参考文献：
  名称：

  Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization of C-Allyl Glycosides

  摘要：

  Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph2MeP)(2)Ir(cod)PF6]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism.

  DOI：

  10.1021/ol060671n

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。