Acetic acid (3aR,4aR,8aR,9S,9aR)-2-methoxy-2-methyl-7-phenyl-hexahydro-[1,3]dioxolo[4',5':5,6]pyrano[3,2-d][1,3]dioxin-9-yl ester | 23262-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Acetic acid (3aR,4aR,8aR,9S,9aR)-2-methoxy-2-methyl-7-phenyl-hexahydro-[1,3]dioxolo[4',5':5,6]pyrano[3,2-d][1,3]dioxin-9-yl ester
• 英文别名: O³-acetyl-O⁴,O⁶-((R)-benzylidene)-O¹,O²-((Ξ)-1-methoxy-ethylidene)-α-D-glucopyranose；O³-Acetyl-O⁴,O⁶-((R)-benzyliden)-O¹,O²-((Ξ)-1-methoxy-aethyliden)-α-D-glucopyranose
• CAS: 23262-88-6；38081-45-7；38081-49-1；56193-00-1
• 化学式: C₁₈H₂₂O₈
• 分子量: 366.368
• InChiKey: QPTUOXNHSVDJSW-CBFUQASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,4aR,8aR,9S,9aR)-2-methoxy-2-methyl-7-phenyl-hexahydro-[1,3]dioxolo[4',5':5,6]pyrano[3,2-d][1,3]dioxin-9-yl ester 在 水 、 溶剂黄146 作用下， 生成 O²,O³-diacetyl-O⁴,O⁶-((R)-benzylidene)-D-glucose
  参考文献：
  名称：

  128.一些“不稳定”系列的聚-O-乙酰基糖基氯的制备和性质

  摘要：

  DOI：

  10.1039/jr9590000636
• 作为产物：
  描述：

  O2,O3-diacetyl-O4,O6-((R)-benzylidene)-β-D-glucopyranosyl chloride 在 甲醇 、 calcium sulfate 、 silver carbonate 作用下， 生成 Acetic acid (3aR,4aR,8aR,9S,9aR)-2-methoxy-2-methyl-7-phenyl-hexahydro-[1,3]dioxolo[4',5':5,6]pyrano[3,2-d][1,3]dioxin-9-yl ester
  参考文献：
  名称：

  128.一些“不稳定”系列的聚-O-乙酰基糖基氯的制备和性质

  摘要：

  DOI：

  10.1039/jr9590000636

文献信息

• A convenient synthesis of the core trisaccharide of the N-glycans
  作者：Zhichao Lu、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li

  DOI：10.1016/j.tetlet.2011.04.060

  日期：2011.6

  A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following

  描述了N-聚糖的核心三糖的方便合成。进行三个单糖结构单元的正交一锅糖基化反应以提供β-葡萄糖基壳二糖，然后通过分子内差向异构化β-葡萄糖苷的C-2位将其转化为β-甘露糖基壳二糖。遵循4，6 - O-亚苄基保护的1，2-原酸酯策略，制备了具有分化的2，3-OH的关键葡糖基供体7c。
• Differentiating the 2,3-diols of glucopyranosides by 4,6-O-benzylidene-protected-1,2-d-glucopyranosylorthoesters strategy
  作者：Guangfa Wang、Zhichao Lu、Ning Ding、Wei Zhang、Peng Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.08.008

  日期：2011.11

  A facile and efficient method to differentiate the 2,3-diols of glucopyranosides based on 1,2-orthoesters strategy was developed. Stable thioglucosides were employed as the starting materials to prepare the corresponding 1,2-orthoesters. When treated with HCl aqueous solution and followed with Et3N, differentiation of the 2,3-diols was efficiently achieved along with the generation of a convertible anomeric hydroxyl group. In addition, an easy and practical method based on NOE was proposed to determine whether the 1,2-orthoesters were endo-type or exo-type. (C) 2011 Elsevier Ltd. All rights reserved.