methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside] | 23193-39-7

• 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: methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside]
• 英文别名: Methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzyliden)-2-desoxy-α-D-glucopyranosid]
• CAS: 23193-39-7
• 化学式: C₂₃H₂₅NO₇
• 分子量: 427.454
• InChiKey: WZOLEFOHPDHWDL-XUDYBECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  92.32
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside] 在 吡啶 、 甲醇 、 水 、 barium methoxide 、 溶剂黄146 、 丙酮 、 silver(l) oxide 、 碘甲烷 作用下， 生成 methyl 2-acetamido-3-O-acetyl-4,6-di-O-methyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  4,6-Di-O-methyl-D-glucosamine Hydrochloride (2-Amino-2-deoxy-4,6-di-O-methyl-D-glucose Hydrochloride)1,2

  摘要：

  4-O-甲基-D-半乳糖胺盐酸盐（2-氨基-2-脱氧-4-O-甲基-D-半乳糖盐酸盐）已从1,6:2,3-二脱水-β-D以结晶形式制备-talopyranose 并通过以下结晶衍生物表征：N-(2'-羟基亚萘基)、甲基 N-乙酰基-α-D-糖苷和甲基 N-乙酰基-3,6-二-O-乙酰基-α-D -糖苷。

  DOI：

  10.1021/ja01631a064
• 作为产物：
  描述：

  甲基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 在 吡啶 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside]
  参考文献：
  名称：

  Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

  摘要：

  Two oligosaccharides, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(l --> 4)-alpha-D-GlcpNAc (I) and alpha-D-Manp-(1 --> 3)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 4)-alpha-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-alpha-D-mannopyranosyl-(l --> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2) -3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(l --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.09.030