(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol | 140926-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol
• CAS: 140926-92-7
• 化学式: C₆₂H₆₄O₁₁
• 分子量: 985.184
• InChiKey: JNYKRTQHUMXGQP-NRRWZGMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.16
• 重原子数：
  73.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120.37
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Tetra-O-benzylvalienamine 、 (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1S,2S,3R,4S,5S)-3,4-Bis-benzyloxy-1-benzyloxymethyl-5-((1S,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexanol
  参考文献：
  名称：

  Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives

  摘要：

  Novel synthetic routes to valiolamine (1a) and N-substituted valiolamine derivatives via branched-chain inosose derivatives are described. (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (3), a branched-chain inosose derivative prepared from D-glucose, 2 has been converted into 1a via the ketoxime 7 followed by hydrogenation. N-Substituted valiolamine derivatives having strong alpha-D-glucosidase inhibitory activity have been synthesized by the direct reductive amination of the branched-chain inosose derivative 3 with an appropriate amino compound to construct the N-substituent moiety, followed by removal of the O-benzyl protecting group. The stereoselective preparation of two representative derivatives, N-[2-hydroxy-1-(hydroxymethyl)ethyl]valiolamine (2a, AO-128)3 and N-[1R,2R)-2-hydroxyclohexyl]valiolamine (2b)3 is described. Application of branched-chain inosose derivatives 3 and 23 to the total synthesis of natural N-substituted valiolamine derivatives validoxylamine G (5a) and validamycin G (6a) is also described.

  DOI：

  10.1021/jo00039a026
• 作为产物：
  描述：

  (1R)-2,3,6-Tri-O-benzyl-1-C-(dichloromethyl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucitol 在 偶氮二异丁腈 、 三正丁基氢锡 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 甲苯 为溶剂， 反应 2.25h， 生成 (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol
  参考文献：
  名称：

  Synthesis of valiolamine and its N-substituted derivatives AO-128, validoxylamine G, and validamycin G via branched-chain inosose derivatives

  摘要：

  Novel synthetic routes to valiolamine (1a) and N-substituted valiolamine derivatives via branched-chain inosose derivatives are described. (1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (3), a branched-chain inosose derivative prepared from D-glucose, 2 has been converted into 1a via the ketoxime 7 followed by hydrogenation. N-Substituted valiolamine derivatives having strong alpha-D-glucosidase inhibitory activity have been synthesized by the direct reductive amination of the branched-chain inosose derivative 3 with an appropriate amino compound to construct the N-substituent moiety, followed by removal of the O-benzyl protecting group. The stereoselective preparation of two representative derivatives, N-[2-hydroxy-1-(hydroxymethyl)ethyl]valiolamine (2a, AO-128)3 and N-[1R,2R)-2-hydroxyclohexyl]valiolamine (2b)3 is described. Application of branched-chain inosose derivatives 3 and 23 to the total synthesis of natural N-substituted valiolamine derivatives validoxylamine G (5a) and validamycin G (6a) is also described.

  DOI：

  10.1021/jo00039a026