2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altritol | 264234-45-9

• 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: 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altritol
• 英文别名: benzyl (2R)-r-2-hydroxymethyl-c-3,c-4-isopropylidenedioxy-t-5-methyl-pyrrolidine-1-carboxylate；benzyl (3aS,4R,6R,6aR)-4-(hydroxymethyl)-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 264234-45-9
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: LIZNEYDHIANHIP-NGFQHRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altritol 在 palladium on activated charcoal Amberlyst-15 H⁺ 、 氢气 作用下， 以 乙醇 为溶剂， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol
  参考文献：
  名称：

  Potent glycosidase inhibitors via hetero Diels-Alder reactions: asymmetric synthesis of 5-methyl-trihydroxypyrrolidines

  摘要：

  Some straightforward chemical transformations of oxazine diol 4, which was obtained from sorbaldehyde 2 by an asymmetric hetero Diels-Alder reaction followed by osmylation, led to the protected dihydroxypyrrolidine-aldehyde 8a and, after basic epimerisation, to 8b. Reduction of the aldehyde moiety and deprotection gave the potent glycosidase inhibitors 2,5,6-trideoxy-2,5-imino-D-altritol and D-allitol 9a and 9b. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00008-6
• 作为产物：
  描述：

  2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altrose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以170 mg的产率得到2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altritol
  参考文献：
  名称：

  Chiral 5-Methyl-trihydroxypyrrolidines—Preparation from 1,2-Oxazines and Glycosidase Inhibitory Properties

  摘要：

  Chemical transformations of chiral 1,2-oxazines 4, 5 gave the 2,5,6-trideoxy-2,5-imino D-alditols 12b, 13b in the D-altritol and D-talitol series, respectively. Basic aldehyde epimerisation led to the D-allitol isomer 15b. Compound 12b is a potent alpha-L-fucosidase and alpha-D-galactosidase inhibitor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01078-9