N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol | 157363-87-6

• 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: N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol
• 英文别名: (3S,4R,5R,6S)-1-benzyl-4,5-bis(phenylmethoxy)azepane-3,6-diol
• CAS: 157363-87-6
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: ZPASIZYEIJMSLL-GWMMUDDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  8
• 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-1,6-dideoxy-1,6-imino-L-iditol 以 二氯甲烷 、 三乙胺 为溶剂， 生成 (3S,4S,5S,6S)-4,5-Bis-benzyloxy-3,6-bis-methanesulfonyloxy-azepane-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis and binding affinities of novel non-peptide mimics of somatostatin/sandostatin®

  摘要：

  Based on molecular modelling studies of Sandostatin(R), sugar-based derivatives I-VI were prepared as potential non-peptide mimics of somatostatin/Sandostatin(R). These compounds displaced 3-[I-125]-Tyr(11)-SRIF-14 from the somatostatin receptor on membranes of rat cerebral cortex with IC50 values between 10 and 15 mu M. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00289-2
• 作为产物：
  描述：

  [(2R,3S,4S,5R)-1,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methylsulfonyloxy-3,4-bis(phenylmethoxy)hexan-2-yl] methanesulfonate 在 盐酸 、 sodium hydroxide 、 高氯酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N-benzyl-3,4-di-O-benzyl-1,6-dideoxy-1,6-imino-L-iditol
  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

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. Part 2 isomerization of polyhydroxylated azepanes
  作者：Lydie Poitout、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0040-4039(96)00097-4

  日期：1996.3

  Isomerization of enantiopure C2-symmetric 3,5-dihydroxyazepane derivatives has been studied. The neighboring nitrogen participation occurs during mesylation to give a chloromethylpiperidine, whereas from the a chiral bridged morpholine structure (1R-(6endo, 7exo)-8-oxa-3-azabicyclo[3.2.1]octane-6,7-diol) is obtained under Mitsunobu conditions.

  对映体纯的C 2对称的3，5-二羟基氮杂环庚烷衍生物的异构化已得到研究。在甲磺酰化过程中发生邻近的氮参与，得到氯甲基哌啶，而从手性桥连的吗啉结构（1R-（6内，7外）-8-氧杂-3-氮杂双环[3.2.1]辛烷-6,7-二醇）是在Mitsunobu条件下获得的。
• 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.
• 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。
• Design, synthesis and binding affinities of novel non-peptide mimics of somatostatin/sandostatin®
  作者：Dominique Damour、Michel Barreau、Jean-Charles Blanchard、Marie-Claude Burgevin、Adam Doble、Frederic Herman、Guy Pantel、Evelyne James-Surcouf、Marc Vuilhorgne、Serge Mignani、Lydie Poitout、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0960-894x(96)00289-2

  日期：1996.7

  Based on molecular modelling studies of Sandostatin(R), sugar-based derivatives I-VI were prepared as potential non-peptide mimics of somatostatin/Sandostatin(R). These compounds displaced 3-[I-125]-Tyr(11)-SRIF-14 from the somatostatin receptor on membranes of rat cerebral cortex with IC50 values between 10 and 15 mu M. Copyright (C) 1996 Elsevier Science Ltd