2-(trimethylsilyl)ethyl (2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 172360-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside；Bn(-2)[Bn(-6)]Gal4Ac(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]Glc(b)-O-EtTMS；[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-4-hydroxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 172360-88-2
• 化学式: C₅₄H₆₆O₁₂Si
• 分子量: 935.196
• InChiKey: XLVNFZQNVGMPQG-FKVROTOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  67
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 、 methyl 4,6-di-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到C₉₀H₉₉NO₁₉Si
  参考文献：
  名称：

  The first synthesis of glycan parts of lactoganglio- and neolactoganglio-series gangliosides

  摘要：

  The glycan parts of lactoganglio- and neolactoganglio-series of gangliosides were synthesized for the first time based on a well-designed synthetic strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00007-7
• 作为产物：
  描述：

  2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 吡啶 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(trimethylsilyl)ethyl (2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-sulfone Neoglycolipids of the 2'-, 3'-, and 6'-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2'-, 3'-, and 6'-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo00127a042

文献信息

• Synthetic sulfated glucuronosyl paragloboside (SGPG) and its use for the detection of autoimmune peripheral neuropathies
  作者：Reynald Chevalier、Benoît Colsch、Carlos Afonso、Nicole Baumann、Jean-Claude Tabet、Jean-Maurice Mallet

  DOI：10.1016/j.tet.2005.10.021

  日期：2006.1

  The sulfated glucuronosyl paragloboside SO4-3-GlcA(beta 1-3)Gal-(beta 1-4)GlcNAc(beta 1-3)Gal-(beta 1-4)Glc beta(1-1')Cer (SGPG) is a specific constituent of the peripheral nervous system involved in human dysimmune neuropathies. Although it is highly immunogenic in human pathology, it is not a major constituent of peripheral nerve in humans. Pure SGPG is very difficult to obtain from natural sources, but is needed for the design of efficient and reproducible immunoassays. We describe a new chemical synthesis of this important glycolipid with a stearic tail, including its complete characterization by mass spectrometry and its use in the detection of autoimmune neuropathies. (c) 2005 Elsevier Ltd. All rights reserved.