benzyl (2S,3S,4S,5R,6S)-6-[(2S)-2-hydroxy-3-[(10R)-10-methyloctadecanoyl]oxypropoxy]-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate | 1421868-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2S,3S,4S,5R,6S)-6-[(2S)-2-hydroxy-3-[(10R)-10-methyloctadecanoyl]oxypropoxy]-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 1421868-81-6
• 化学式: C₅₆H₇₆O₁₀
• 分子量: 909.213
• InChiKey: HMIYEZRIZWSDBN-XBMCCXEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  66
• 可旋转键数：
  35
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S,4S,5R,6S)-6-[(2S)-2-hydroxy-3-[(10R)-10-methyloctadecanoyl]oxypropoxy]-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate 在 4-二甲氨基吡啶 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 20% palladium hydroxide-activated charcoal 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 1-O-((R)-10-methylstearyl)-2-O-palmityl-sn-glyceryl α-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria

  摘要：

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.

  DOI：

  10.1021/jo302508e
• 作为产物：
  描述：

  benzyl (1-O-((R)-10-methylstearyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 benzyl (2S,3S,4S,5R,6S)-6-[(2S)-2-hydroxy-3-[(10R)-10-methyloctadecanoyl]oxypropoxy]-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria

  摘要：

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.

  DOI：

  10.1021/jo302508e