8-methoxycarbonyloctyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside | 194603-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside
• CAS: 194603-28-6
• 化学式: C₂₂H₃₇NO₁₀
• 分子量: 475.536
• InChiKey: VTYKCRBNGNDDDK-MSEOUXRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  149.68
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 在 苯磺酰胺 、 β(1-4)gal-t 、 sodium cacodylate buffer 、 sodium methylate 、 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 、 magnesium chloride 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成
  参考文献：
  名称：

  Glycosyl-transferase catalyzed assemblage of sialyl-lewis x -saccharopeptides

  摘要：

  A series of glycohexopyranuronic acids are coupled to glucosamines to give 'disaccharides' which have the natural N-acetyl group of the glcNAc-moiety replaced by various sugar acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for beta(1-4)galactosyl-transferase, alpha(2-3)sialyl-transferase, and fucosyl-transferase VI. The enzymes transfer successively galactose, sialic acid, and fucose from the corresponding donors onto these acceptor substrates-despite the far reaching alterations-regio- and stereospecifically in the expected manner to yield a new class of compounds, the sialyl-Lewis(x)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00107-2
• 作为产物：
  描述：

  9-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-allyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-nonanoic acid methyl ester 在 四(三苯基膦)钯 、 丙二酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到8-methoxycarbonyloctyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl-transferase catalyzed assemblage of sialyl-lewis x -saccharopeptides

  摘要：

  A series of glycohexopyranuronic acids are coupled to glucosamines to give 'disaccharides' which have the natural N-acetyl group of the glcNAc-moiety replaced by various sugar acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for beta(1-4)galactosyl-transferase, alpha(2-3)sialyl-transferase, and fucosyl-transferase VI. The enzymes transfer successively galactose, sialic acid, and fucose from the corresponding donors onto these acceptor substrates-despite the far reaching alterations-regio- and stereospecifically in the expected manner to yield a new class of compounds, the sialyl-Lewis(x)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00107-2

文献信息

• Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors
  作者：Oliver Schwardt、Gabi Baisch、Reinhold Öhrlein

  DOI：10.1016/s0968-0896(01)00086-4

  日期：2001.7

  A series of D- and L-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These 'disaccharides'. in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for beta (1-4)-galactosyl-transferase and alpha (1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates. despite the far reaching, alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides. (C) 2001 Elsevier Science Ltd. All rights reserved.