3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose | 218961-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose
• CAS: 218961-08-1
• 化学式: C₂₈H₂₅NO₇
• 分子量: 487.509
• InChiKey: YQSLUUDSTVOGNU-ZKVDKWSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.53
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose 在 二氯二茂铪 、 二甲氨基三氟化硫 、 silver perchlorate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit

  摘要：

  The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn(44) was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00342-2
• 作为产物：
  描述：

  2-[(2R,4aR,6S,7R,8R,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 在 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit

  摘要：

  The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn(44) was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00342-2

文献信息

• Synthesis and Biological Evaluation of a Chitobiose-Based Peptide <i>N</i>-Glycanase Inhibitor Library
  作者：Martin D. Witte、Danielle Horst、Emmanuel J. H. J. Wiertz、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1021/jo801906s

  日期：2009.1.16

  Peptide N-glycanase (PNGase), the enzyme responsible for the deglycosylation of N-linked glycoproteins, has an active site related to that of cysteine proteases. Chitiobiose was equipped with electrophilic traps often used in cysteine protease inhibitors, and the resulting compounds were evaluated as PNGase inhibitors. We found that the electrophilic trap of the inhibitor has a great influence on the potency of the compounds with the chloromethyl ketone inhibitor being the first potent C-glycoside-based PNGase inhibitor.