2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose | 222040-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose
• 英文别名: 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-galactopyranosyl)-α-D-mannopyranose；2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl β-D-galactopyranosyl)-6-O-acetyl-α-D-mannopyranose；Gal2Ac3Ac4Ac6Ac(b1-4)a-Man2Ac3Ac6Ac；[(2R,3R,4S,5S,6S)-4,5-diacetyloxy-6-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 222040-92-8
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: QBBPOGFLHMTZQB-IWJSCKEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232.02
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose 在 咪唑 、 三甲基乙酰氯 、 三氯化磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.83h， 生成 triethylammonium 3-azidopropyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-acetyl-α-D-mannopyranosylphosphate
  参考文献：
  名称：

  A Ferrier glycosylation/cis-dihydroxylation strategy to synthesizeLeishmaniaspp. lipophosphoglycan-associated βGal(1,4)Man disaccharide

  摘要：

  通过费里尔糖基化/顺式二羟基化策略合成了利什曼病种细胞表面脂磷聚糖（LPG）中的 Galβ(1→4)Man 二糖。

  DOI：

  10.1039/d2ra05158c
• 作为产物：
  描述：

  N-(间甲苯基)甲磺酰胺 在 吡啶 、 sodium dihydrogenphosphate 、 四氧化锇 、 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 、 N-甲基吗啉氧化物 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 29.25h， 生成 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  A Ferrier glycosylation/cis-dihydroxylation strategy to synthesizeLeishmaniaspp. lipophosphoglycan-associated βGal(1,4)Man disaccharide

  摘要：

  通过费里尔糖基化/顺式二羟基化策略合成了利什曼病种细胞表面脂磷聚糖（LPG）中的 Galβ(1→4)Man 二糖。

  DOI：

  10.1039/d2ra05158c

文献信息

• 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。
• Synthesis of the phosphodisaccharide repeat of antigenic lipophosphoglycan of Leishmania donovani parasite
  作者：Mani Upreti、Ram A. Vishwakarma

  DOI：10.1016/s0040-4039(99)00231-2

  日期：1999.3

  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.