N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol | 157363-86-5

• 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: N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: (3S,4R,5R,6R)-1-benzyl-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)piperidin-3-ol
• CAS: 157363-86-5
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: DXXRHAUKWPLHBB-HVWQDESWSA-N

物化性质

• 沸点：
  583.5±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 在 钯 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 15.0h， 以100%的产率得到1-脱氧野尻霉素
  参考文献：
  名称：

  D-甘露醇合成1-脱氧野oji霉素及其类似物的多羟基哌啶和氮杂环丙烷

  摘要：

  可以容易地从D-甘露醇获得的D-甘露醇和L -iditol双环氧化物是通过一个环氧官能团的亲核开口随后自发的分子内环闭合而合成多羟基化哌啶和氮杂环庚烷的方便底物。使用这种策略，制备了1-脱氧野oji霉素和类似物。

  DOI：

  10.1016/s0040-4039(00)76888-2
• 作为产物：
  描述：

  N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-2,6-di-O-methanesulfonyl-D-glucitol 在 甲醇 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 N-benzyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  氮杂糖的合成作为糖苷酶的有效抑制剂。

  摘要：

  通过C2-对称双环氧化物的氨基杂环化反应，由D-甘露醇合成了一系列对映体纯的氮杂糖（2,5-dideoxy-2、5-imino-D-甘露醇，1-deoxynojirimycin，1-deoxymannojirimycin和相关化合物）。在少数情况下随后进行环异构化。这些化合物已被评估为几种糖苷酶（α-和β-D-葡糖苷酶，α-D-甘露糖苷酶和α-L-岩藻糖苷酶）的抑制剂。抑制研究显着地表明，多羟基化的氮杂环庚烷是糖苷酶的抑制剂，Ki在微摩尔范围内。

  DOI：

  10.1016/s0968-0896(96)00266-0

文献信息

• Synthesis of azasugars. Part 1 isomerization of polyhydroxylated piperidines
  作者：Lydie Poitout、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0040-4039(96)00096-2

  日期：1996.3

  and l-gulitol undergo easy isomerization, mainly either by ring contraction, or either by SN2 inversion at C2. This isomerization performed by bis-hydroxyl activation allows to access to 2,5-dideoxy-2,5-imino-l-iditol, 5-epi-DNJ, DMDP, and DMJ.

  α-和谷氨醇容易发生异构化，主要是通过环收缩或通过C 2处的SN 2转化。通过双羟基活化进行的这种异构化允许获得2,5-二脱氧-2,5-亚氨基-1-ID醇，5-epi-DNJ，DMDP和DMJ。
• Syntheses and Evaluation as Glycosidase Inhibitor of 1,5-Dideoxy-1,5-imino-D-glucitol Analogs of Salacinol, a Potent α-Glucosidase Inhibitor Isolated from Ayurvedic Medicine, Salacia reticulata
  作者：Osamu Muraoka、Genzoh Tanabe、Takanori Hatanaka、Toshie Minematsu、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.3987/com-08-s(d)61

  日期：——

  N-Alkylated deoxynojirimycin (10) bearing the same alkyl chain as salacinol (1), a potent alpha-glucosidase inhibitor isolated from Ayurvedic traditional medicine, Salacia reticulata, was found to inhibit both rat intestinal maltase and sucrase as strong as 1, while 10 has been reported to be inactive against glucoamylase G2 from Aspergillus niger. Its O-desulfate (12) was also found active against these enzymes, and characteristic sulfate anion moiety of I was found not essential for the alpha-glucosidase inhibitory activity.
• Polyhydroxylated piperidines and azepanes from D-mannitol synthesis of 1-deoxynojirimycin and analogues
  作者：Lydie Poitout、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/s0040-4039(00)76888-2

  日期：1994.5

  D-mannitol and L-iditol bis-epoxides, easily obtained from D-mannitol, are convenient substrates for the synthesis of polyhydroxylated piperidines and azepanes, via a nucleophilic opening of one epoxy function followed by a spontaneous intramolecular ring closure. Using this strategy 1-deoxynojirimycin and analogues were prepared.

  可以容易地从D-甘露醇获得的D-甘露醇和L -iditol双环氧化物是通过一个环氧官能团的亲核开口随后自发的分子内环闭合而合成多羟基化哌啶和氮杂环庚烷的方便底物。使用这种策略，制备了1-脱氧野oji霉素和类似物。
• Synthesis of azasugars as potent inhibitors of glycosidases
  作者：Yves Le Merrer、Lydie Poitout、Jean-Claude Depezay、Isabelle Dosbaa、Sabine Geoffroy、Marie-José Foglietti

  DOI：10.1016/s0968-0896(96)00266-0

  日期：1997.3

  A series of enantiomerically pure azasugars (2,5-dideoxy-2, 5-imino-D-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from D-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (alpha- and beta-D-glucosidases

  通过C2-对称双环氧化物的氨基杂环化反应，由D-甘露醇合成了一系列对映体纯的氮杂糖（2,5-dideoxy-2、5-imino-D-甘露醇，1-deoxynojirimycin，1-deoxymannojirimycin和相关化合物）。在少数情况下随后进行环异构化。这些化合物已被评估为几种糖苷酶（α-和β-D-葡糖苷酶，α-D-甘露糖苷酶和α-L-岩藻糖苷酶）的抑制剂。抑制研究显着地表明，多羟基化的氮杂环庚烷是糖苷酶的抑制剂，Ki在微摩尔范围内。