2-(trimethylsilyl)ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-4,6-O-DTBS-α-D-galactopyranosyl-(1-4)-(methyl 5-methoxycarbonylamino-5,7-N,O-DTBS-8,9-O-DTBS-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosydonate)-(2-3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 1196690-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-4,6-O-DTBS-α-D-galactopyranosyl-(1-4)-(methyl 5-methoxycarbonylamino-5,7-N,O-DTBS-8,9-O-DTBS-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosydonate)-(2-3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: dimethyl (4S,4aR,6S,8S,8aR)-8-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-8-[(2S,3R,4S,5S)-3,4-diacetyloxy-5-[(1R)-1,2-diacetyloxyethyl]oxolan-2-yl]oxy-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxy]-6-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-5-hydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-2,2-ditert-butyl-4-[(4R)-2,2-ditert-butyl-1,3,2-dioxasilolan-4-yl]-4a,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3,2]oxazasiline-1,6-dicarboxylate
• CAS: 1196690-81-9
• 化学式: C₁₁₅H₁₆₅NO₃₄Si₄
• 分子量: 2217.9
• InChiKey: ZYMFIODIJIZCBW-GSZHAECGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.73
• 重原子数：
  154
• 可旋转键数：
  52
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  375
• 氢给体数：
  1
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-4,6-O-DTBS-α-D-galactopyranosyl-(1-4)-(methyl 5-methoxycarbonylamino-5,7-N,O-DTBS-8,9-O-DTBS-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosydonate)-(2-3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以91%的产率得到2-(trimethylsilyl)ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-α-D-galactopyranosyl-(1-4)-5-methoxycarbonylamino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosydonate-(2-3,1-4)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the starfish ganglioside AG2 pentasaccharide

  摘要：

  This Letter reports the first synthesis of the AG2 pentasaccharide, using silylene-oxazolidinone double-locked sialic acid building blocks. The di-DTBS-protected sialic acid building block was easily prepared and readily activated with NIS and TfOH to provide the sialylated lactose unit in good yield with moderate selectivity. After obtaining the trisaccharide unit, the oxazolidinone-protected C4-OH on the sialic acid residue was readily deprotected by treatment with NaOMe. Coupling with the galactofuranosyl beta(1-3)galactopyranosyl fluoride building block produced the desired AG2 pentasaccharide in a highly stereoselective manner. Finally, the desired AG2 pentasaccharide was obtained in good yield following global deprotection. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.071
• 作为产物：
  描述：

  2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-4,6-O-DTBS-α-D-galactopyranosyl trichloroacetimidate 、 2-(trimethylsilyl)ethyl (methyl) 5-methoxycarbonylamino-5,7-N,O-DTBS-8,9-O-DTBS-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosidonate-(2-3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到2-(trimethylsilyl)ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1-3)-2-O-benzyl-4,6-O-DTBS-α-D-galactopyranosyl-(1-4)-(methyl 5-methoxycarbonylamino-5,7-N,O-DTBS-8,9-O-DTBS-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosydonate)-(2-3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the starfish ganglioside AG2 pentasaccharide

  摘要：

  This Letter reports the first synthesis of the AG2 pentasaccharide, using silylene-oxazolidinone double-locked sialic acid building blocks. The di-DTBS-protected sialic acid building block was easily prepared and readily activated with NIS and TfOH to provide the sialylated lactose unit in good yield with moderate selectivity. After obtaining the trisaccharide unit, the oxazolidinone-protected C4-OH on the sialic acid residue was readily deprotected by treatment with NaOMe. Coupling with the galactofuranosyl beta(1-3)galactopyranosyl fluoride building block produced the desired AG2 pentasaccharide in a highly stereoselective manner. Finally, the desired AG2 pentasaccharide was obtained in good yield following global deprotection. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.071

文献信息

• Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques
  作者：Shinya Hanashima、Ken-ichi Sato、Yuko Naito、Hiromu Takematsu、Yasunori Kozutsumi、Yukishige Ito、Yoshiki Yamaguchi

  DOI：10.1016/j.bmc.2010.03.062

  日期：2010.6

  Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galf beta(1-3)Galp alpha(1-4)Neu5Ac alpha(2-3)Galp beta(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing (1)H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galp alpha(1-4)Neu5Ac alpha(2-3)Galp unit. (C) 2010 Elsevier Ltd. All rights reserved.