2,6-anhydro-3,4,5,7-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-gluco-heptose | 140397-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-3,4,5,7-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-gluco-heptose
• 英文别名: (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)methanal；(2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside) methanal；(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane-2-carbaldehyde
• CAS: 140397-45-1
• 化学式: C₃₅H₃₆O₆
• 分子量: 552.667
• InChiKey: KKPOREZWWWRARY-HPRFQDQJSA-N

物化性质

• 沸点：
  673.6±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-gluco-heptose 在 sodium tetrahydroborate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 生成 (2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl alcohol
  参考文献：
  名称：

  一种合成α-和β- c-糖基醛的有效方法

  摘要：

  描述了从单一碳水化合物前体合成α-和β- C-糖基醛的实用方法。

  DOI：

  10.1016/s0040-4039(00)77703-3
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 以40%的产率得到2,6-anhydro-3,4,5,7-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-gluco-heptose
  参考文献：
  名称：

  [EN] SYNTHETIC C-GLYCOLIPID AND ITS USE FOR TREATING CANCER INFECTIOUS DISEASES AND AUTOIMMUNE DISEASES
  [FR] C-GLYCOLIPIDE DE SYNTHESE ET UTILISATION DE CELUI-CI POUR LE TRAITEMENT DU CANCER, DES MALADIES INFECTIEUSES ET DES MALADIES AUTO-IMMUNES

  摘要：

  公开号：

  WO2003105769A3

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。
• Synthesis of Novel Donor Mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as Potential Transferase Inhibitors
  作者：Andreas Schäfer、Joachim Thiem

  DOI：10.1021/jo990766l

  日期：2000.1.1

  For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside

  对于半乳糖，N-乙酰氨基葡糖和N-乙酰半乳糖胺的酶促转移，使用UDP-Gal（1），UDP-GlcNAc（2）和UDP-GalNAc（3），并且UDP用作反馈抑制剂。在本文中，描述了作为潜在转移酶抑制剂的新型UDP-糖类似物4、5和6的合成。与天然衍生物1-3中的异头氧相反，化合物4-6在糖和核苷部分之间具有C-糖苷羟基亚甲基键。
• Synthesis and Conformational Analysis of (α-D-Galactosyl)phenylmethane and α-,β-Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin
  作者：Maria Kolympadi、Marco Fontanella、Chiara Venturi、Sabine André、Hans-Joachim Gabius、Jesús Jiménez-Barbero、Pierre Vogel

  DOI：10.1002/chem.200801394

  日期：2009.3.9

  To bend about: The conformations of three phenyl‐C‐galactosides in solution were evaluated by using theoretical calculations and NMR spectroscopic studies. The α‐CF2 derivative (see scheme) showed significant flexibility of the pyranose ring and around the pseudoanomeric center, whereas the other two analogues more closely resemble the natural galactosides. Regardless, all three compounds bind to a

  弯腰：通过使用理论计算和NMR光谱研究评估了溶液中三种苯基C-半乳糖苷的构象。α-CF 2衍生物（参见方案）显示吡喃糖环和围绕pseudoanomeric中心的显著灵活性，而其它两个类似物更接近于天然半乳糖苷。无论如何，所有这三种化合物都与植物凝集素结合。
• Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis
  作者：Szabolcs Sipos、István Jablonkai

  DOI：10.1016/j.carres.2011.04.019

  日期：2011.9

  carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl glycal and 2-deoxy glycosyl derivatives were stable during isolation and storage 1-C-glycosyl formaldehydes in the gluco, galacto and manno series were sensitive and decomposition occurred by 2-alkyloxy elimination

  使用DIBAL-H进行各种保护的糖基氰化物的还原水解以形成醛亚胺铝烷中间体，然后将其在中等酸性条件下水解以提供相应的醛衍生物。尽管1-C-甲酰基糖基和2-脱氧糖基衍生物在分离和存储过程中是稳定的，但葡萄糖，半乳糖和甘露糖系列中的1-C-糖基甲醛很敏感，并且通过2-烷氧基消除发生了分解。开发了一种使用N，N'-二苯基乙二胺以稳定形式捕集这些醛的一锅法。糖基氰化物的还原水解以方便的方式提供了有价值的醛结构单元，可用于合成复杂的C-糖苷。
• [EN] SYNTHETIC C-GLYCOLIPID AND ITS USE FOR TREATING CANCER INFECTIOUS DISEASES AND AUTOIMMUNE DISEASES<br/>[FR] C-GLYCOLIPIDE DE SYNTHESE ET UTILISATION DE CELUI-CI POUR LE TRAITEMENT DU CANCER, DES MALADIES INFECTIEUSES ET DES MALADIES AUTO-IMMUNES
  申请人：——

  公开号：WO2003105769A3

  公开（公告）日：2004-04-08