(2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine | 217298-94-7

• 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: (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine
• CAS: 217298-94-7
• 化学式: C₃₅H₃₉NO₄
• 分子量: 537.699
• InChiKey: IMWWFEASEOOHAO-BPHVYFQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine 在 palladium dihydroxide 盐酸 、 sodium periodate 、 氢气 、 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 55.75h， 生成 n-propyl 2-acetamido-2,3-dideoxy-4-O-(β-D-galactopyranosyl)-3-amino-3-N-{2-[N-(β-L-homofuconojirimycinyl)]ethyl}-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a New Class of N-Linked Lewis and LacNAc Analogues as Potential Inhibitors of Human Fucosyltransferases:  A General Method for the Incorporation of an Iminocyclitol as a Transition-State Mimetic of the Donor Sugar to the Acceptor

  摘要：

  A short and effective synthesis of N-linked di- and trisaccharides is described. In a high-yielding reaction sequence, the glucosamine derivative 1 was transformed to the 3-azido-2,3-dideoxy sugar 2e under excellent stereocontrol. The LacNAc analogue 4d was synthesized as a single isomer in three steps starting from 2e. In a one-pot procedure, iminocyclitol 5 was transformed into aldehyde 6 and successfully used for reductive amination with 4c and 2f to give trisaccharide 8a and disaccharide 7a, respectively. This procedure represents a general strategy for the incorporation of an iminocyclitol as a transition-state mimic of the donor sugar moiety to the acceptor.

  DOI：

  10.1021/jo981245l
• 作为产物：
  描述：

  (2R,3R,4R,5R,6S)-1-Benzyl-3,4,5-tris-benzyloxy-2-benzyloxymethyl-6-methyl-piperidine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 以96%的产率得到(2S,3R,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)piperidine
  参考文献：
  名称：

  Synergistic Inhibition of Human α-1,3-Fucosyltransferase V

  摘要：

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.

  DOI：

  10.1021/ja960274f

文献信息

• Chemoenzymatic synthesis of iminocyclitol derivatives: A useful library strategy for the development of selective fucosyltransfer enzymes inhibitors
  作者：Ralf Wischnat、Richard Martin、Shuichi Takayama、Chi-Huey Wong

  DOI：10.1016/s0960-894x(98)00617-9

  日期：1998.12

  A chemoenzymatic strategy has been developed for the synthesis of libraries of iminocyclitol derivatives for the discovery of new and selective fucosidase inhibitors. (C) 1998 Published by Elsevier Science Ltd. Ail rights reserved.