8-methoxycarbonyl-octyl-2-O-benzyl-α-D-glucopyranoside | 161453-85-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-methoxycarbonyl-octyl-2-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 9-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-phenylmethoxyoxan-2-yl]oxynonanoate
• CAS: 161453-85-6
• 化学式: C₂₃H₃₆O₈
• 分子量: 440.534
• InChiKey: WHWAOJFDDGLGOL-IFPLKCGESA-N

物化性质

• 沸点：
  587.135±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.206±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyl-octyl-2-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以82%的产率得到8-methoxycarbonyloctyl α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α-d-Glcp-(1 → 2)-α-d-Glcp-(1 → 3)-α-d-Glcp-O-(CH2)8COOCH3 for use in the assay of α-glucosidase I activity

  摘要：

  The chemical synthesis of alpha-D-Glcp-(1 --> 2)-alpha-D-Glc p-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (9), a substrate specific for cr-glucosidase I, is reported. This enzyme removes the terminal alpha-D-Glcp unit to produce alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K-m value (1.3 mM). The fluorescent label allows visual detection of 2-3 pmol of product by TLC. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00242-x
• 作为产物：
  描述：

  8-methoxycarbonyloctyl-3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以2.56 g的产率得到8-methoxycarbonyl-octyl-2-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α-d-Glcp-(1 → 2)-α-d-Glcp-(1 → 3)-α-d-Glcp-O-(CH2)8COOCH3 for use in the assay of α-glucosidase I activity

  摘要：

  The chemical synthesis of alpha-D-Glcp-(1 --> 2)-alpha-D-Glc p-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (9), a substrate specific for cr-glucosidase I, is reported. This enzyme removes the terminal alpha-D-Glcp unit to produce alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K-m value (1.3 mM). The fluorescent label allows visual detection of 2-3 pmol of product by TLC. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00242-x

文献信息

• Modified
  申请人：Alberta Research Council

  公开号：US05929037A1

  公开（公告）日：1999-07-27

  Disclosed is the trisaccharide .alpha.-D-Glcp-(1-2)-.alpha.-D-Glcp-(1-3)-.alpha.-D-Glcp and compounds related thereto as well as pharmaceutical compositions thereof.

  揭示了三糖α-D-Glcp-(1-2)-α-D-Glcp-(1-3)-α-D-Glcp及其相关化合物以及其药物组合物。
• MODIFIED ALPHA-D-Glcp-(1-2)-ALPHA-D-Glcp-(1-3)-ALPHA-D-Glcp-ANALOGUES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0837867B1

  公开（公告）日：2001-08-16
• US5929037A
  申请人：——

  公开号：US5929037A

  公开（公告）日：1999-07-27
• Synthesis of α-d-Glcp-(1 → 2)-α-d-Glcp-(1 → 3)-α-d-Glcp-O-(CH2)8COOCH3 for use in the assay of α-glucosidase I activity
  作者：Christine H. Scaman、Ole Hindsgaul、Monica M. Palcic、Om P. Srivastava

  DOI：10.1016/s0008-6215(96)00242-x

  日期：1996.12

  The chemical synthesis of alpha-D-Glcp-(1 --> 2)-alpha-D-Glc p-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (9), a substrate specific for cr-glucosidase I, is reported. This enzyme removes the terminal alpha-D-Glcp unit to produce alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K-m value (1.3 mM). The fluorescent label allows visual detection of 2-3 pmol of product by TLC. (C) 1996 Elsevier Science Ltd.