(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-piperidine | 225927-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-piperidine
• 英文别名: (2S,3S,4R,5R,6R)-2-[2-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethynyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine
• CAS: 225927-87-7
• 化学式: C₆₃H₆₅NO₉
• 分子量: 980.21
• InChiKey: YKODLBNYKANVQF-RIDXZFEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  73
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-piperidine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.5h， 以80%的产率得到azaGlc-β-(1->6)-C-Glc*HCl
  参考文献：
  名称：

  A Short and Flexible Route to Aza-β-(1→6)-C-disaccharides: Selective α-Glycosidase Inhibitors

  摘要：

  The syntheses of azaMan-beta-(1-->6)-C-Glc (4), azaGlc-beta-(1-->6)-C-Glc (5), and azaGal-beta-(1-->6)-C-Glc (6) based upon double reductive amination of acetylenic carbohydrate-derived diketones is described. The required diketones are obtained by addition of the acetylenic sugar anion derived from dibromoolefin 7 to benzyl-protected mannopyranolactone, glucopyranolactone, or galactopyranolactone, followed by reduction of the ketose and oxidation of the resulting diol. Ensuing double reductive amination and hydrogenolysis affords the target compounds in reasonable to good yields. Enzyme inhibition tests show that neither of the three compounds 4, 5, and 6 inhibit beta-glycosidases, while moderate to good inhibitory activities were found on alpha-glycosidases, the most active being 6 (alpha-galactosidase: K-i = 0.092 mu M).

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1185::aid-ejoc1185>3.0.co;2-a
• 作为产物：
  描述：

  5-内酯 在 sodium tetrahydroborate 、 正丁基锂 、 3 A molecular sieve 、 TEA 、 ammonium formate 、 sodium cyanoborohydride 、 二甲基亚砜 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 (2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-piperidine
  参考文献：
  名称：

  A Short and Flexible Route to Aza-β-(1→6)-C-disaccharides: Selective α-Glycosidase Inhibitors

  摘要：

  The syntheses of azaMan-beta-(1-->6)-C-Glc (4), azaGlc-beta-(1-->6)-C-Glc (5), and azaGal-beta-(1-->6)-C-Glc (6) based upon double reductive amination of acetylenic carbohydrate-derived diketones is described. The required diketones are obtained by addition of the acetylenic sugar anion derived from dibromoolefin 7 to benzyl-protected mannopyranolactone, glucopyranolactone, or galactopyranolactone, followed by reduction of the ketose and oxidation of the resulting diol. Ensuing double reductive amination and hydrogenolysis affords the target compounds in reasonable to good yields. Enzyme inhibition tests show that neither of the three compounds 4, 5, and 6 inhibit beta-glycosidases, while moderate to good inhibitory activities were found on alpha-glycosidases, the most active being 6 (alpha-galactosidase: K-i = 0.092 mu M).

  DOI：

  10.1002/(sici)1099-0690(199905)1999:5<1185::aid-ejoc1185>3.0.co;2-a