2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate | 324041-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-3)Man2Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 324041-35-2
• 化学式: C₄₈H₄₄Cl₃NO₁₈
• 分子量: 1029.23
• InChiKey: VEATYKFOTHQQSB-DLTYFHBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate 、 allyl (3,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以66.3%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

  摘要：

  Two oligosaccharides, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(l --> 4)-alpha-D-GlcpNAc (I) and alpha-D-Manp-(1 --> 3)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 4)-alpha-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-alpha-D-mannopyranosyl-(l --> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2) -3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(l --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.09.030
• 作为产物：
  描述：

  在 1,8-diaza-bicyclo[5.4.0]undecene 、 氨 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a mannose heptasaccharide of the pathogenic yeast, Candida glabrata IFO 0622 strain

  摘要：

  An effective synthesis of the mannose heptasaccharide existing in the pathogenic yeast, Candida glabrata IFO 0622 strain was achieved via TMSOTf-promoted condensation of a tetrasaccharide donor 13 with a trisaccharide acceptor 16, followed by deprotection. The tetrasaccharide 13 was constructed by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (7) with allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (10), followed by deallylation and trichloroacetimadation. The trisaccharide 16 was obtained by coupling of 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate with 10, and subsequent 6-O-deacetylation. The disaccharide 7 was prepared through coupling of perbenzoylated mannosyl trichloroacetimidate with 4,6-O-benzylidene-1,2-O-ethylidene-beta-D-mannopyranose, then simultaneous debenzylidenation and deethylidenation, and subsequent acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The disaccharide 10 was obtained by self-condensation of 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-beta-D-mannopyranose, followed by selective 2-O-deacetylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00162-3

文献信息

• Zhu; Kong, Synlett, 2000, # 12, p. 1783 - 1787
  作者：Zhu、Kong

  DOI：——

  日期：——