2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose | 171815-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose
• 英文别名: (2Z,3aS,4S,5S,6R,7S,7aS)-2-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]imino-3a,4,5,6,7,7a-hexahydro-3H-1,3-benzoxazole-4,5,6,7-tetrol
• CAS: 171815-18-2
• 化学式: C₄₁H₄₆N₂O₁₀
• 分子量: 726.824
• InChiKey: NQKYXDIZKCCOMG-QDRFPUIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  161
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 、 、 1-Deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a 2-Aminohexahydrobenzoxazole Analog Related to Trehazolin

  摘要：

  2-Aminohexahydrobenzoxazole analogue 1a, related to trehazolin (2) was synthesized using the Ferrier reaction as a key step. The structural elucidation of this compound by NMR analysis indicated that it is an inseparable mixture of three components (1a-c) which in turn stems from the propensity of 1a to partially undergo both transcyclization (1a --> 1b) of the aminooxazoline between the hydroxy group at the C-1 position of aminocyclitol in the aglycon moiety and the hydroxy group at the C-2 position of D-glucose moiety and successive transformation (1b --> 1c) of the D-glucose moiety from a pyranose to a furanose structure.

  DOI：

  10.1021/jo00124a023
• 作为产物：
  描述：

  Methyl 3,4-bis-O-(methoxymethyl)-2,6-bis-O-(p-toluenesulfonyl)-α-D-glucopyranoside 在 palladium dihydroxide 、 mercury(II) trifluoroacetate 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 cerium(III) chloride 、 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 乙酸酐 、 四丁基碘化铵 、 sodium hydride 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 248.5h， 生成 2,3,4,6-Tetra-O-benzyl-1-deoxy-1-<<<3aS-(3aα,4α,5α,6β,7α,7aα)>-4,5,6,7-tetrahydroxy-3a,4,5,6,7,7a-hexahydrobenzoxazol-2-yl>amino>-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of a 2-Aminohexahydrobenzoxazole Analog Related to Trehazolin

  摘要：

  2-Aminohexahydrobenzoxazole analogue 1a, related to trehazolin (2) was synthesized using the Ferrier reaction as a key step. The structural elucidation of this compound by NMR analysis indicated that it is an inseparable mixture of three components (1a-c) which in turn stems from the propensity of 1a to partially undergo both transcyclization (1a --> 1b) of the aminooxazoline between the hydroxy group at the C-1 position of aminocyclitol in the aglycon moiety and the hydroxy group at the C-2 position of D-glucose moiety and successive transformation (1b --> 1c) of the D-glucose moiety from a pyranose to a furanose structure.

  DOI：

  10.1021/jo00124a023