1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranose | 414878-05-0

• 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: 1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-5,6-diacetyloxy-2-(acetyloxymethyl)-4-benzoyloxyoxan-3-yl] benzoate
• CAS: 414878-05-0
• 化学式: C₂₆H₂₆O₁₁
• 分子量: 514.486
• InChiKey: PULZICAPRYZBFI-IOCWQACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 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
• 作为产物：
  描述：

  乙酸酐 、 3,4-di-O-benzoyl-D-mannopyranose 以 吡啶 为溶剂， 反应 5.0h， 以100%的产率得到1,2,6-tri-O-acetyl-3,4-di-O-benzoyl-α-D-mannopyranose
  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

• A highly efficient synthesis of an octasaccharide, the repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum
  作者：Jun Ning、Linsen Heng、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00117-9

  日期：2002.7

  A highly concise and effective synthesis of the mannose octasaccharide repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum was achieved via 6-O-glycosylation of a tetrasaccharide acceptor with a tetrasaccharide donor, followed by deprotection. The key tetrasaccharide (11) was constructed by selective 6-O-glycosylation of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside with 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate. The tetrasaccharide acceptor (13) was obtained by selective 6-O-deacetylation of 11, while the tetrasaccharide donor 12 was obtained by deallylation of 11, followed by trichloroacetimidation. (C) 2002 Elsevier Science Ltd. All rights reserved.