(2R,3S,4S,5R,6S)-dimethyl (3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-yl)-methylenephosphonate | 908836-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S,5R,6S)-dimethyl (3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-yl)-methylenephosphonate
• CAS: 908836-27-1
• 化学式: C₃₀H₃₈NO₇P
• 分子量: 555.608
• InChiKey: ONVMWAZSTDRUNX-KTBGKDHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-dimethyl (3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-yl)-methylenephosphonate 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以98%的产率得到((2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-hydroxymethyl-piperidin-2-ylmethyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of the Dimethyl Ester of 1‐Deoxy‐l‐Idonojirimycin‐1‐Methylenphosphonate: A New Approach to Iminosugar Phosphonates

  摘要：

  1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12.[GRAPHICS]

  DOI：

  10.1080/07328300600731990
• 作为产物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-6-O-t-butyldiphenylsilyl-D-glucitol 在 甲醇 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 四丁基氟化铵 、 sodium 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 (2R,3S,4S,5R,6S)-dimethyl (3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-yl)-methylenephosphonate
  参考文献：
  名称：

  Synthesis of the Dimethyl Ester of 1‐Deoxy‐l‐Idonojirimycin‐1‐Methylenphosphonate: A New Approach to Iminosugar Phosphonates

  摘要：

  1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of the aldehyde at C-1 of compound 10 with dimethyl methylenephosphonate anion, conversion of the azide into an amino group, and finally cyclization of the aminoalcohol 12.[GRAPHICS]

  DOI：

  10.1080/07328300600731990