allyl 6-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranoside | 524951-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4R,5S,6S)-2-(acetyloxymethyl)-4-benzoyloxy-5-hydroxy-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 524951-96-0
• 化学式: C₂₅H₂₆O₉
• 分子量: 470.476
• InChiKey: OBUKAOYAXWUBIF-GYLCGTKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 allyl 6-O-acetyl-3,4-di-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92%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-6-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  First syntheses of d-mannose penta- and decasaccharides, the repeating unit and its dimer of the cell-wall mannan of Candida kefyr IFO 0586

  摘要：

  alpha-D-Mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose and alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)]-alpha-D-marmopyranosyl-(1-->6)-[alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranosyl-(1-->2)]-alpha-D-mannopyranose, the repeating unit and its dimer of the cell wall mannan of the pathogenic yeast Candida kefyr IFO 0586, have been efficiently synthesized via their allyl glycosides by using allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside, allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside, and allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside as synthons. The blocked pentasaccharide was regio- and stereoselectively prepared by coupling of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, and then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate in a one-pot manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00216-7
• 作为产物：
  描述：

  2,6-di-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 allyl 6-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a mannose heptasaccharide existing in baker's yeast, Saccharomyces cerevisiae X2180-1A wild-type strain

  摘要：

  A mannose heptasaccharide existing in baker's yeast, Saccharomyces cerevisiae X2180-1A wild-type strain, was effectively synthesized as its allyl glycoside via TMSOTf-promoted condensation of a disaccharide donor 13 with a pentasaccharide acceptor 12, followed by deprotection. The pentasaccharide 12 was constructed by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichioroacetimidate (9) with allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside (10), followed by deacetylation. The tetrasaccharide 9 was obtained by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (5) with allyl 3,4,6-tri-O-benzoyl-a-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (6), followed by deallylation and trichloroacetimidation. The disaccharides 6 and 13 were readily obtained by known methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00402-0