5-amino-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal | 264234-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-amino-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal
• 英文别名: (1R)-1-[(4S,5R)-5-[(1R)-1-aminoethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethoxyethanol
• CAS: 264234-39-1
• 化学式: C₁₁H₂₃NO₅
• 分子量: 249.307
• InChiKey: GAEOUNSYJDYONY-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 amberlyst-15 、 Amberlyst-15 H⁺ 、 氢气 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 52.0h， 生成 (2S,3S,4R,5R)-3,4-dihydroxy-2-hydroxymethyl-5-methylpyrrolidine
  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：

  benzyl (3R,4R,5R,6R)-6-(dimethoxymethyl)-4,5-dihydroxy-3-methyloxazinane-2-carboxylate 在 palladium on activated charcoal Amberlyst-15 (H⁺) 、 氢气 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 5-amino-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal
  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.