3-acetamido-1,3,5-trideoxy-1,5-imino-D-glucitol | 122371-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-acetamido-1,3,5-trideoxy-1,5-imino-D-glucitol
• 英文别名: N-[(2R,3R,4R,5S)-3,5-Dihydroxy-2-(hydroxymethyl)-4-piperidinyl]acetamide；N-[(2R,3R,4R,5S)-3,5-dihydroxy-2-(hydroxymethyl)piperidin-4-yl]acetamide
• CAS: 122371-75-9
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: IDIKCIZORGTYPF-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-acetamido-2,4,6-tri-O-acetyl-5-amino-3,5-dideoxy-D-glucono-1,5-lactam 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以77%的产率得到3-acetamido-1,3,5-trideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol

  摘要：

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.016

文献信息

• KISO, MAKOTO;KITAGAWA, MASAYUKI;ISHIDA, HIDEHARU;HASEGAWA, AKIRA, J. CARBOHYDR. CHEM., 10,(1991) N, C. 25-45
  作者：KISO, MAKOTO、KITAGAWA, MASAYUKI、ISHIDA, HIDEHARU、HASEGAWA, AKIRA

  DOI：——

  日期：——
• JP1079192A
  申请人：——

  公开号：JP1079192A

  公开（公告）日：1989-03-24
• A stereocontrolled synthesis of 3-acetamido-1,3,5-trideoxy- and 1,3,5,6-tetradeoxy-1,5-imino-d-glucitol
  作者：Ondřej Šimák、Jan Staněk、Jitka Moravcová

  DOI：10.1016/j.carres.2009.03.016

  日期：2009.5

  3-Acetamido-5-amino-3,5,6-trideoxy-D-glucono-1,5-lactam and 3-acetamido-5-amino-3,5-dideoxy-D-glucono-1,5-lactam were synthesized from corresponding 3-acetamido-3-deoxy-beta-D-glucopyranosides in 63% and 35% overall yield, respectively. Acetylation followed by reduction led to the title 3-acetamido-3-deoxy derivatives of both deoxynojirimycin and 1,6-dideoxynojirimycin. The procedure developed is useful for a multi-gram scale. (C) 2009 Elsevier Ltd. All rights reserved.