3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride | 277310-81-3

• 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-glucopyranosyl fluoride
• 英文别名: 2-[(2R,4aR,6S,7R,8R,8aS)-6-fluoro-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 277310-81-3
• 化学式: C₂₈H₂₄FNO₆
• 分子量: 489.5
• InChiKey: IRRCUOQMXDPTRL-HUZYSJDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 在 二氯二茂铪 、 silver perchlorate 、 乙二胺 作用下， 以 甲醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 2.0h， 生成 O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-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-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 咪唑 、 4-二甲氨基吡啶 、 二甲氨基三氟化硫 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
  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

• 10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c
  作者：Martin-Lomas, Manuel、Flores-Mosquera, Maria、Chiara, Jose Luis

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1547::aid-ejoc1547<3.0.co;2-c

  日期：——
• Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit
  作者：Hironobu Hojo、Jun Watabe、Yoshiaki Nakahara、Yuko Nakahara、Yukishige Ito、Kazuki Nabeshima、Bryan P Toole

  DOI：10.1016/s0040-4039(01)00342-2

  日期：2001.4

  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.