2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altrose | 188242-66-2

• 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-altrose
• 英文别名: benzyl (2S)-r-2-formyl-c-3,c-4-isopropylidenedioxy-t-5-methyl-pyrrolidine-1-carboxylate；benzyl (3aS,4S,6R,6aR)-4-formyl-2,2,6-trimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 188242-66-2
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: FUVLBVYHLZWCMJ-NGFQHRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 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-altrose 在 palladium on activated charcoal sodium tetrahydroborate 、 Amberlyst-15 (H⁺) 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.5h， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol
  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 dimethylacetal 在 Amberlyst-15 (H⁺) 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altrose
  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

文献信息

• 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.