allyl 3,4-di-O-benzoyl-α-D-mannopyranoside | 414878-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4-di-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4R,5S,6S)-4-benzoyloxy-5-hydroxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 414878-07-2
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: KVFLWBORFAJTAI-ZNOYZCKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 3,4-di-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 Bz(-2)[Bz(-3)][Bz(-4)]Man6Ac(a1-6)[Bz(-3)][Bz(-4)]Man2Ac(a)-O-allyl
  参考文献：
  名称：

  Facile syntheses of d-mannose hexa- and nonasaccharides: the di- and trimer of the trisaccharide repeating unit of the cell-wall mannans of Epidermophyton floccosum, Trychophyton mentagrophytes, Microsporum canis and related species of Microsporum

  摘要：

  A highly efficient strategy for the preparation Of D-mannose hexa- and nonasaccharides, the dimer and trimer of the alpha-D-Manp-(1 --> 6)-[alpha-D-Manp-(1 --> 2)-]D-Manp trisaccharide repeating unit of the cell-wall mannans from the fungi Epidermophyton flovcosum, Trychophyton mentagrophytes, Microsporum canis, ill. cookei and V racemosum, has been developed Using 1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranose (6) as the key synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02232-8
• 作为产物：
  描述：

  allyl 2,6-di-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以96%的产率得到allyl 3,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Facile syntheses of d-mannose hexa- and nonasaccharides: the di- and trimer of the trisaccharide repeating unit of the cell-wall mannans of Epidermophyton floccosum, Trychophyton mentagrophytes, Microsporum canis and related species of Microsporum

  摘要：

  A highly efficient strategy for the preparation Of D-mannose hexa- and nonasaccharides, the dimer and trimer of the alpha-D-Manp-(1 --> 6)-[alpha-D-Manp-(1 --> 2)-]D-Manp trisaccharide repeating unit of the cell-wall mannans from the fungi Epidermophyton flovcosum, Trychophyton mentagrophytes, Microsporum canis, ill. cookei and V racemosum, has been developed Using 1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranose (6) as the key synthon. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02232-8

文献信息

• First syntheses of d-mannose penta- and decasaccharides, the repeating unit and its dimer of the cell-wall mannan of Candida kefyr IFO 0586
  作者：Ying Xing、Jun Ning

  DOI：10.1016/s0957-4166(03)00216-7

  日期：2003.5

  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.