N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea | 171815-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea
• CAS: 171815-17-1
• 化学式: C₄₁H₄₈N₂O₁₀S
• 分子量: 760.906
• InChiKey: LBJIUXAZYPTYMS-ZYYLIXAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  171.36
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea 在 palladium dihydroxide 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 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 、 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 246.5h， 生成 N-<<1S-(1α,2β,3α,4β,5β,6α)>-1,2,3,4,5-Pentahydroxycyclohex-6-yl>-N'-(2,3,4,6-tetra-O-α-D-glucopyranosyl)thiourea
  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