methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate-(1→2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose | 1607444-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate-(1→2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose
• CAS: 1607444-99-4
• 化学式: C₃₇H₄₀O₁₄
• 分子量: 708.716
• InChiKey: RIANGARGIDHPLX-WQOJSWGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate-(1→2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose 在 甲醇 、 sodium methylate 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.67h， 生成 [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis of benzyl protected β-d-GlcA-(1→2)-α-d-Man thioglycoside building blocks for construction of Cryptococcus neoformans capsular polysaccharide structures

  摘要：

  In a project targeting the synthesis of large oligosaccharide structures corresponding to the Cryptococcus neoformans GXM capsular polysaccharide, an easy access to thiodisaccharide building blocks comprising a beta-linked glucuronic acid moiety and a 6-O-acetyl group was required. Several pathways to such building blocks have been investigated, addressing the problem of constructing a beta-linked glucuronic acid residue protected with groups that are orthogonal to a primary acetyl group. Two efficient routes have been developed, one using benzoylated glucosyl donors to form the beta-linkage followed by a change of protecting groups to benzyls and subsequent introduction of the carboxyl function and the acetyl group. The second route explored the possibility to achieve beta-selectivity using glucuronyl donors without acyl protecting groups. BF3- etherate promoted glycosylations with benzyl (2,3,4-tri-O-benzyl-alpha-D-glucupyranosyl)uronate trichloroacetimidate in the presence of nitrile solvents and at low temperatures reproducibly gave good yields of disaccharides with high beta-selectivity. Furthermore, the use of recently reported glucuronyl thioglycoside donors protected with a cyclic 2,4-silylene acetal was found to represent another efficient and completely beta-selective way to desired disaccharide building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.022
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate 、 1,6-anhydro-4-O-benzyl-3-O-(2-naphthyl)methyl-β-D-mannopyranose 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate-(1→2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis of benzyl protected β-d-GlcA-(1→2)-α-d-Man thioglycoside building blocks for construction of Cryptococcus neoformans capsular polysaccharide structures

  摘要：

  In a project targeting the synthesis of large oligosaccharide structures corresponding to the Cryptococcus neoformans GXM capsular polysaccharide, an easy access to thiodisaccharide building blocks comprising a beta-linked glucuronic acid moiety and a 6-O-acetyl group was required. Several pathways to such building blocks have been investigated, addressing the problem of constructing a beta-linked glucuronic acid residue protected with groups that are orthogonal to a primary acetyl group. Two efficient routes have been developed, one using benzoylated glucosyl donors to form the beta-linkage followed by a change of protecting groups to benzyls and subsequent introduction of the carboxyl function and the acetyl group. The second route explored the possibility to achieve beta-selectivity using glucuronyl donors without acyl protecting groups. BF3- etherate promoted glycosylations with benzyl (2,3,4-tri-O-benzyl-alpha-D-glucupyranosyl)uronate trichloroacetimidate in the presence of nitrile solvents and at low temperatures reproducibly gave good yields of disaccharides with high beta-selectivity. Furthermore, the use of recently reported glucuronyl thioglycoside donors protected with a cyclic 2,4-silylene acetal was found to represent another efficient and completely beta-selective way to desired disaccharide building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.01.022