1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose | 222040-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose
• 英文别名: 1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-galactopyranosyl)-α-D-mannopyranose；O¹,O²,O³,O⁶-Tetraacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose；Gal2Ac3Ac4Ac6Ac(b1-4)a-Man1Ac2Ac3Ac6Ac；[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 222040-87-1
• 化学式: C₂₈H₃₈O₁₉
• 分子量: 678.598
• InChiKey: WOTQVEKSRLZRSX-HPIYTGOMSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  683.055±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.370±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose 在 platinum(IV) oxide 正丁基锂 、 氢气 、 二甲胺 作用下， 以 乙腈 为溶剂， -78.0~-20.0 ℃ 、344.74 kPa 条件下， 反应 16.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-phosphonooxy-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of the phosphodisaccharide repeat of antigenic lipophosphoglycan of Leishmania donovani parasite

  摘要：

  Synthesis of the immunologically important and structurally unusual phosphodisaccharide repeat unit (Galp1,4 beta-Manp-1 alpha-phosphate) of the lipophosphoglycan cell surface GPI molecule of the protozoan parasite Leishmania donovani has been carried out using lactose as the starting material. The synthesis provides a short and stereoselective route for the preparation of this phosphosaccharide in a preparative scale. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00231-2
• 作为产物：
  描述：

  2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-altropyranosyl)-β-D-glucopyranose 、 乙酸酐 在 硫酸 、 溶剂黄146 作用下， 生成 1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  Syntheses of Epi-lactose and Lactose

  摘要：

  DOI：

  10.1021/ja01260a031

文献信息

• Iodine and Its Interhalogen Compounds: Versatile Reagents in Carbohydrate Chemistry V. Synthesis of 1,2-trans-Linked 1-Thioglycosides from the Per-O-acetylated Glycoses
  作者：K. P. Ravindranathan Kartha、Robert Field

  DOI：10.1080/07328309808002346

  日期：1998.5.1

  derivative, but the reaction is not stereospecific. Moreover, in the latter reactions a portion of the starting material remains unchanged even on prolonged reaction. With β-D-glucose pentaacetate (11) as the starting material, its epimerisation occurred during the reaction and therefore the recovered starting material was of α-D-configuration. In addition, the methyl disulphide-hexamethyldisilane system has

  摘要在环境温度下用（烷基/芳硫基）三甲基硅烷和碘处理过-O-乙酰化的单糖和二糖会以非常高的收率形成相应的1,2-反式-1-硫代糖苷。在较高沸点的硫醇如乙硫醇的情况下，该反应可以在硫醇本身而不是甲硅烷基化衍生物的存在下有效地进行，但是该反应不是立体特异性的。此外，在后一反应中，即使在长时间反应下，一部分起始原料也保持不变。以β-D-葡萄糖五乙酸酯（11）为起始原料，其差向异构发生在反应过程中，因此回收的起始原料为α-D构型。此外，已经发现，甲基二硫化物-六甲基乙硅烷体系可以代替昂贵的（甲硫基）-三甲基硅烷而成为一种有效且廉价的替代品。1.致敬日本岐阜大学长谷川晃教授。2.有关第四部分，请参阅KPRK。
• 1-Oxabicyclic β-lactams as new inhibitors of elongating MPT–a key enzyme responsible for assembly of cell-surface phosphoglycans of Leishmania parasite
  作者：Dipali Ruhela、Patrali Chatterjee、Ram A. Vishwakarma

  DOI：10.1039/b418247b

  日期：——

  New iminosugars (1-oxabicyclic β-lactam disaccharides) have been synthesized as inhibitors of elongating α-D-mannosyl phosphate transferase (eMPT), a key enzyme involved in the iterative biosynthesis of cell-surface phosphoglycans of the Leishmania parasite. The design is based on a transition-state model for this remarkable enzyme that transfers intact α-D-mannosyl-phosphate from GDP-Man. Since these phosphoglycans are unique to Leishmania and are essential for its infectivity and survival, their biosynthetic pathway has emerged as a novel target for anti-leishmanial drug and vaccine design.

  我们合成了新的亚氨基糖（1-氧代双环δ²-内酰胺二糖），作为拉长δ±-D-甘露糖基磷酸转移酶（eMPT）的抑制剂，eMPT 是一种参与利什曼寄生虫细胞表面磷聚糖迭代生物合成的关键酶。该设计基于这种从 GDP-Man 转移完整 δ±-D-mannosyl-phosphate 的非凡酶的过渡状态模型。由于这些磷聚糖是利什曼原虫特有的，对其感染性和存活至关重要，因此它们的生物合成途径已成为抗利什曼原虫药物和疫苗设计的新目标。