allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside | 374078-98-5

• 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: allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-2-(acetyloxymethyl)-4,5-dibenzoyloxy-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 374078-98-5
• 化学式: C₃₂H₃₀O₁₀
• 分子量: 574.584
• InChiKey: ZUJYNIDKANUCAQ-JABZFZETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以2.9 g的产率得到allyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  First synthesis of the immunodominant β-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus

  摘要：

  beta-Galf-(1 --> 5)-p-Galf-(1 --> 6)-alpha-Manp-(1 --> 6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra- O-benzoyl-beta-D-galactofuranosyl-(1 --> 5)-2-O-acetyl- 3,6-di-O-benzoyl-beta-D -galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.019
• 作为产物：
  描述：

  烯丙醇 、 1,6-di-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到allyl 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
  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