1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol | 16647-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol
• 英文别名: (3S,4R,5R,6S)-3,4,5,6-tetrahydroxyazepane；3(S),4(R),5(R),6(S)-tetrahydroxyazepane；(2S,3R,4R,5S)-tetrahydroxyazepane；1,6-dideoxy-1,6-imino-L-iditol；azepane；(3s,4r,5r,6s)-Azepane-3,4,5,6-Tetrol
• CAS: 16647-61-3
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: MRFFNLOQLBWKPJ-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 在 palladium on activated charcoal 氢气 、 ammonium formate 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 80.0 ℃ 、551.58 kPa 条件下， 反应 33.67h， 生成 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol
  参考文献：
  名称：

  Concise and practical synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6-iminosugars

  摘要：

  The syntheses of (2S,3R,4R,5R) and (2S,3R,4R,5S)-1,6-dideoxy-1,6 iminosugars 1a and 1b, respectively, from D-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive amination of amino-aldehyde. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(03)00177-7

文献信息

• 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。
• C2-Symmetrical tetrahydroxyazepanes as inhibitors of glycosidases and HIV/FIV proteases
  作者：Xinhua Qian、Francisco Morís-Varas、Michael C. Fitzgerald、Chi-Huey Wong

  DOI：10.1016/s0968-0896(96)00218-0

  日期：1996.12

  C2-Symmetrical tetrahydroxyazepanes were synthesized as inhibitors for glycosidases. Tetrahydroxyazepane 1 is a non-specific inhibitor of various glycosidases, while compounds 2, 3 and 4 specifically inhibit beta-N-acetylglucosaminidase, beta-glucosidase, and alpha-fucosidase, respectively, with Ki in the micromolar range. Compound 1 is not an inhibitor of HIV/FIV proteases, but its 3,6-difluorobenzyl

  合成C 2-对称的四羟基氮杂环庚烷作为糖苷酶的抑制剂。四羟基氮杂环庚烷1是各种糖苷酶的非特异性抑制剂，而化合物2、3和4分别以微摩尔范围的Ki特异性抑制β-N-乙酰氨基葡萄糖苷酶，β-葡萄糖苷酶和α-岩藻糖苷酶。化合物1不是HIV / FIV蛋白酶的抑制剂，但是其3,6-二氟苄基衍生物是这两种酶的中度抑制剂。
• Syntheses of tetrahydroxyazepanes from chiro-inositols and their evaluation as glycosidase inhibitors
  作者：Gavin F Painter、Paul J Eldridge、Andrew Falshaw

  DOI：10.1016/j.bmc.2003.10.003

  日期：2004.1

  Two pairs of C(2)-symmetric tetrahydroxyazepanes [(-), (+)-1 and (-), (+)-2] have been synthesized from the enantiomeric chiro-inositols and evaluated as glycosidase inhibitors. Alternative syntheses of ido-tetrahydroxyazepanes (-)- and (+)-2 from myo-inositol were also developed. The key synthetic transformations were glycol fission and cyclization of the derived dialdehydes by double reductive amination

  从对映体手性肌醇合成了两对C（2）-对称的四羟基氮杂环庚烷[（-），（+）-1和（-），（+）-2]，并被评估为糖苷酶抑制剂。还开发了由肌醇制备的偶氮-四羟基氮杂环庚烷（-）-和（+）-2的替代合成方法。关键的合成转化是乙二醇裂变和通过双还原胺化对衍生的二醛进行环化。D-甘露糖四羟基氮杂环庚烷[（-）-1]显示出对α-L-岩藻糖苷酶和β-D-半乳糖苷酶的选择性抑制，而对映体[（+）-1]是α-D-半乳糖苷酶的选择性抑制剂。相比之下，L-ido-四羟基氮杂环庚烷（+）-2是一种广谱的己糖苷酶抑制剂，但未显示任何已报道的己糖胺酶抑制作用。它的对映异构体（-）-2是一种不良的己糖苷酶抑制剂。
• Total syntheses of (+)-castanospermine and (+)-deoxynojirimycin
  作者：Ronald C. Bernotas、Bruce Ganem

  DOI：10.1016/s0040-4039(00)99830-7

  日期：1984.1