2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allitol | 264234-50-6

• 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-allitol
• 英文别名: (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine；benzyl (2S)-r-2-hydroxymethyl-t-3,t-4-isopropylidenedioxy-c-5-methyl-pyrrolidine-1-carboxylate；benzyl (3aS,4S,6R,6aR)-4-(hydroxymethyl)-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 264234-50-6
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: LIZNEYDHIANHIP-BEAPCOKYSA-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-allitol 在 Amberlyst-15 (H⁺) 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以90%的产率得到2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-allitol
  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
• 作为产物：
  描述：

  2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altrose 在 sodium tetrahydroborate 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allitol
  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

文献信息

• Preparation and Biological Evaluation of Pyrrolidinediols and Pyrrolidine N-Oxides from D-Ribose Using the Nitrone Approach
  作者：Andreas M. Palmer、Volker Jäger

  DOI：10.1002/1099-0690(200107)2001:13<2547::aid-ejoc2547>3.0.co;2-h

  日期：2001.7

  olidine 1-oxides with various 2-substituents into the free diols and, by reduction, into the corresponding pyrrolidinediols (iminoglycitols) is described. The pyrrolidine N-oxides were derived from D-ribose via unsaturated hydroxylamines, with the key steps of nitrone addition and Cope−House cyclization as described earlier. The biological activity of these compounds with respect to glycosidase inhibition

  描述了具有各种 2-取代基的 3,4-异亚丙基二氧基-5-甲基吡咯烷 1-氧化物转化为游离二醇，并通过还原转化为相应的吡咯烷二醇（亚氨基糖醇）。吡咯烷 N-氧化物通过不饱和羟胺从 D-核糖衍生而来，关键步骤是硝酮加成和 Cope-House 环化，如前所述。检查了这些化合物在糖苷酶抑制方面的生物活性；虽然所有测试的吡咯烷 N-氧化物都被证明是无活性的，但一些新的亚氨基多元醇对 α-L-岩藻糖苷酶和 α-D-葡萄糖苷酶表现出中等活性，Ki 值为 30-40 μM。
• Potent glycosidase inhibitors via hetero Diels-Alder reactions: asymmetric synthesis of 5-methyl-trihydroxypyrrolidines
  作者：A. Defoin、Th. Sifferlen、J. Streith、I. Dosbaâ、M.-J. Foglietti

  DOI：10.1016/s0957-4166(97)00008-6

  日期：1997.2

  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.
• Chiral 5-Methyl-trihydroxypyrrolidines—Preparation from 1,2-Oxazines and Glycosidase Inhibitory Properties
  作者：Thierry Sifferlen、Albert Defoin、Jacques Streith、Didier Le Nouën、Céline Tarnus、Isabelle Dosbaâ、Marie-José Foglietti

  DOI：10.1016/s0040-4020(99)01078-9

  日期：2000.2

  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.