2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose | 374078-97-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose
• 英文别名: [(2R,3R,4S,5S,6S)-5-acetyloxy-3,4-dibenzoyloxy-6-hydroxyoxan-2-yl]methyl benzoate
• CAS: 374078-97-4
• 化学式: C₂₉H₂₆O₁₀
• 分子量: 534.519
• InChiKey: GVJDOCSNJBTHCX-OEZIKMGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 caesium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Bz(-3)[Bz(-4)][Bz(-6)]Man(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Man(a)-O-Bz
  参考文献：
  名称：

  从克氏锥虫的脂质中含有不饱和脂肪酸的生物活性糖基磷脂酰肌醇的化学合成。

  摘要：

  DOI：

  10.1002/anie.200502779
• 作为产物：
  描述：

  1,2-di-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose 在 苄胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88.4%的产率得到2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranose
  参考文献：
  名称：

  SYNTHESIS OF A MANNOTETRAOSE—THE REPEATING UNIT OF THE CELL-WALL MANNANS OF MICROSPORUM GYPSEUM AND RELATED SPECIES OF TRYCHOPHYTON

  摘要：

  A tetrasaccharide, alpha -D-mannopyranosyl-(1 -->2)-alpha -D-mannopyranosyl-(1 -->6)-alpha -D-mannopyranosyl-(1 -->6)-D-maanopyranose (1), the repeating unit of the cell-wall mannans of Microsporum gypseum and related species of Trychophyton, was synthesized using 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (5) and 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (13) as the glycosyl donors in "the inverse Schmidt 'procedure.

  DOI：

  10.1081/car-100104864

文献信息

• Unexpected Stereocontrolled Access to 1α,1′β-Disaccharides from Methyl 1,2-Ortho Esters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1021/jo202335n

  日期：2012.1.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1 alpha,1'beta-disaccharides, upon treatment with BF3 center dot Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.
• SYNTHESIS OF A MANNOTETRAOSE—THE REPEATING UNIT OF THE CELL-WALL MANNANS OF <i>MICROSPORUM GYPSEUM</i> AND RELATED SPECIES OF <i>TRYCHOPHYTON</i>
  作者：Linsen Heng、Jun Ning、Fanzuo Kong

  DOI：10.1081/car-100104864

  日期：2001.4.30

  A tetrasaccharide, alpha -D-mannopyranosyl-(1 -->2)-alpha -D-mannopyranosyl-(1 -->6)-alpha -D-mannopyranosyl-(1 -->6)-D-maanopyranose (1), the repeating unit of the cell-wall mannans of Microsporum gypseum and related species of Trychophyton, was synthesized using 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (5) and 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha -D-mannopyranosyl trichloroacetimidate (13) as the glycosyl donors in "the inverse Schmidt 'procedure.
• The Chemical Synthesis of Bioactive Glycosylphosphatidylinositols fromTrypanosoma cruzi Containing an Unsaturated Fatty Acid in the Lipid
  作者：Dmitry V. Yashunsky、Vladimir S. Borodkin、Michael A. J. Ferguson、Andrei V. Nikolaev

  DOI：10.1002/anie.200502779

  日期：2006.1.9