Benzyl 4-C-tert-butyloxycarbonylaminomethyl-4-deoxy-α-L-xylo-pyranoside | 383173-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 4-C-tert-butyloxycarbonylaminomethyl-4-deoxy-α-L-xylo-pyranoside
• 英文别名: tert-butyl N-[[(3S,4R,5S,6S)-4,5-dihydroxy-6-phenylmethoxyoxan-3-yl]methyl]carbamate
• CAS: 383173-72-6
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: CUXDYZJUCZKREE-XUWVNRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Benzyl 4-C-tert-butyloxycarbonylaminomethyl-4-deoxy-α-L-xylo-pyranoside 在 10percent Pd/C 氢气 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 16.08h， 生成 (2R,3S,4R,5S)-5-Aminomethyl-tetrahydro-pyran-2,3,4-triol; hydrochloride 、 (2S,3S,4R,5S)-5-Aminomethyl-tetrahydro-pyran-2,3,4-triol; hydrochloride 、 5-epi-Noeuromycin hydrochloride
  参考文献：
  名称：

  Efficient Synthesis of Isofagomine and Noeuromycin

  摘要：

  Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha -D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21 % overall yield.

  DOI：

  10.1002/1521-3765(20010903)7:17<3744::aid-chem3744>3.0.co;2-3
• 作为产物：
  描述：

  (4R,4s)-苄基-4-脱氧-4-c-硝基甲基-beta-d-阿拉伯糖苷 在 10percent Pd/C 氢气 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 生成 Benzyl 4-C-tert-butyloxycarbonylaminomethyl-4-deoxy-α-L-xylo-pyranoside
  参考文献：
  名称：

  Efficient Synthesis of Isofagomine and Noeuromycin

  摘要：

  Starting from D-arabinose the synthesis of the very strong glycosidase inhibitors isofagomine (2) and noeuromycin (3) was achieved in six and seven steps, respectively. Keystep in the reaction sequence is the application of an efficient C-4 oxidation method to benzyl alpha -D-arabino-pyranoside. Subsequent Henry reaction of the obtained aldoketose with nitromethane provided the required branched carbohydrate precursors, which gave access to 2 and 3 in 17-21 % overall yield.

  DOI：

  10.1002/1521-3765(20010903)7:17<3744::aid-chem3744>3.0.co;2-3