12-azidododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1036637-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-azidododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-(12-azidododecoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1036637-18-9
• 化学式: C₂₀H₃₈N₄O₆
• 分子量: 430.545
• InChiKey: GHAQFIZXRDLLNW-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  12-azidododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以90%的产率得到12-aminododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical and enzymatic synthesis of neoglycolipids in the presence of cyclodextrins

  摘要：

  The efficiency of cyclodextrins (CDs), alpha-CD, beta-CD and gamma-CD, for the blotting of hydrophobic substrates to water-soluble polymers and for the synthesis of neoglycolipids using glycosyltransferase is described. CDs did not disturb HPLC purification and did not bring lather. These merits are superior to surfactants commonly used in such a case. The utility of CDs as a novel and efficient supporting material for enzymatic glycosylation is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.103
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以97%的产率得到12-azidododecyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical and enzymatic synthesis of neoglycolipids in the presence of cyclodextrins

  摘要：

  The efficiency of cyclodextrins (CDs), alpha-CD, beta-CD and gamma-CD, for the blotting of hydrophobic substrates to water-soluble polymers and for the synthesis of neoglycolipids using glycosyltransferase is described. CDs did not disturb HPLC purification and did not bring lather. These merits are superior to surfactants commonly used in such a case. The utility of CDs as a novel and efficient supporting material for enzymatic glycosylation is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.103

文献信息

• Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition
  作者：Koji Matsuoka、Hiroki Yamaguchi、Tatsuya Kohzu、Jun-Ichi Sakamoto、Tetsuo Koyama、Ken Hatano、Shigeto Yamamoto、Tsutomu Mori、Kenichi Hatanaka

  DOI：10.1016/j.tetlet.2012.10.004

  日期：2012.12

  The Le(x) glycoside having an N-3 moiety at the omega position, which was prepared by using living cells from GlcNAcO(CH2)(12)N-3 as a starting material, was efficiently introduced into a trivalent-type carbosilane core scaffold by means of Huisgen cycloaddition reaction to yield the corresponding glycocluster having three Le(x) moieties at each end. Structural elucidation of the product was performed by a combination of NMR and mass spectroscopic analyses, and the results of the analyses supported the structure of the glycocluster. Evaluation of the glycocluster was carried out using Lotus lectin as a model lectin. Environmental changes of tryptophan residues located at or near the binding sites of Lotus lectin caused fluorescence intensity change. (C) 2012 Elsevier Ltd. All rights reserved.
• Chemical and enzymatic synthesis of neoglycolipids in the presence of cyclodextrins
  作者：Izuru Nagashima、Hiroki Shimizu、Takahiko Matsushita、Shin-Ichiro Nishimura

  DOI：10.1016/j.tetlet.2008.03.103

  日期：2008.5

  The efficiency of cyclodextrins (CDs), alpha-CD, beta-CD and gamma-CD, for the blotting of hydrophobic substrates to water-soluble polymers and for the synthesis of neoglycolipids using glycosyltransferase is described. CDs did not disturb HPLC purification and did not bring lather. These merits are superior to surfactants commonly used in such a case. The utility of CDs as a novel and efficient supporting material for enzymatic glycosylation is also discussed. (C) 2008 Elsevier Ltd. All rights reserved.