methyl tri-O-benzoyl-α-D-arabinopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl tri-O-benzoyl-α-D-arabinopyranoside
• 英文别名: [(3R,4R,5S,6S)-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: BMICZGNBUCUNFZ-LAWREARLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinopyranoside 在 吡啶 、 硫酸 、 copper(II) sulfate 、 丙酮 作用下， 生成 methyl 2-O-methanesulfonyl-α-D-arabinopyranoside
  参考文献：
  名称：

  The Preparation of Crystalline 2-O-Methylsulfonyl-D-arabinose and Some of Its Derivatives

  摘要：

  DOI：

  10.1021/ja01552a056
• 作为产物：
  描述：

  1,3,5-三苯甲酰基-D-呋喃核糖 在 吡啶 、 甲醇 、 二氯甲烷 、 sodium methylate 作用下， 生成 methyl tri-O-benzoyl-α-D-arabinopyranoside
  参考文献：
  名称：

  Evidence that the Supposed 3,5-Di-O-benzoyl-1,2-O-(1-hydroxybenzylidene)-α-D- ribose is Actually 1,3,5-Tri-O-benzoyl-α-D-ribose

  摘要：

  DOI：

  10.1021/ja01599a048

文献信息

• Vesparioside from the Marine SpongeSpheciospongia vesparia, the First Diglycosylceramide with a Pentose Sugar Residue
  作者：Valeria Costantino、Ernesto Fattorusso、Concetta Imperatore、Alfonso Mangoni

  DOI：10.1002/ejoc.200400543

  日期：2005.1

  The marine sponge Spheciospongia vesparia produces vesparioside (1a), a diglycosylated glycosphingolipid which is the first example of a natural diglycosylceramide with a pentose sugar residue. The structure of vesparioside was mostly determined by extensive spectroscopic analysis but determination of the nature of the alkyl chains and elucidation of the absolute stereochemistry of the sugars and of

  海海绵 Spheciospongia vesparia 产生 vesparioside (1a)，一种双糖基化的鞘糖脂，它是第一个带有戊糖残基的天然双糖基神经酰胺的例子。vesparioside 的结构主要通过广泛的光谱分析确定，但确定烷基链的性质和阐明糖和神经酰胺的绝对立体化学需要化学降解。在这方面，这里首次采用了一种改进和简化的用于微尺度化学降解鞘糖脂的程序。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• The Reaction of Tribenzoyl-β-D-arabinopyranosyl Bromide and Tribenzoyl-α-D-xylopyranosyl Bromide with Methanol
  作者：Hewitt G. Fletcher、C. S. Hudson

  DOI：10.1021/ja01165a093

  日期：1950.9
• Sinularioside, a triacetylated glycolipid from the Indonesian soft coral Sinularia sp., is an inhibitor of NO release
  作者：Masteria Yunovilsa Putra、Angela Ianaro、Elisabetta Panza、Giorgio Bavestrello、Carlo Cerrano、Ernesto Fattorusso、Orazio Taglialatela-Scafati

  DOI：10.1016/j.bmcl.2012.02.102

  日期：2012.4

  Chemical analysis of the Indonesian soft coral Sinularia sp. (order Alcyonacea, family Alcyoniidae) afforded a known glucosylcerebroside of the sarcoehrenoside-type and sinularioside (2), a new naturally triacetylated glycolipid containing two alpha-D-arabinopyranosyl residues and a myristyl alcohol unit. Their complete stereostructures were solved by interpretation of MS and NMR data along with CD analysis of degradation products. Sinularioside proved to moderately inhibit LPS-induced NO release, providing interesting clues into the poorly understood structure-activity relationships for anti-inflammatory glycolipids. (C) 2012 Elsevier Ltd. All rights reserved.