2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 1064663-27-9

• 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-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S,6R)-6-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-3,4-dibenzoyloxy-5-hydroxyoxan-2-yl]oxymethyl]-3,4,5-tribenzoyloxyoxan-2-yl]oxymethyl]-4,5-dibenzoyloxy-6-(2-trimethylsilylethoxy)oxan-3-yl] benzoate
• CAS: 1064663-27-9
• 化学式: C₁₀₇H₁₁₄O₂₉Si₂
• 分子量: 1920.24
• InChiKey: GPPDJVIYQYXLNJ-SZPGFZFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.08
• 重原子数：
  138
• 可旋转键数：
  45
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  341
• 氢给体数：
  1
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以95.6%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-4-O-acetyl-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neutral glycosphingolipids from Zygomycetes

  摘要：

  Novel neutral glycosphingolipids (NGSLs) containing Gal-alpha l -> 6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different froth those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis alpha-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethane-sulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.019
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-1-thio-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 4 A molecular sieve 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以76.6%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-2,3-di-O-benzoyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of neutral glycosphingolipids from Zygomycetes

  摘要：

  Novel neutral glycosphingolipids (NGSLs) containing Gal-alpha l -> 6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different froth those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis alpha-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethane-sulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.019

文献信息

• Synthesis of neutral glycosphingolipids from Zygomycetes
  作者：Noriyasu Hada、Junko Oka、Kyoko Hakamata、Kenji Yamamoto、Tadahiro Takeda

  DOI：10.1016/j.carres.2008.04.019

  日期：2008.9

  Novel neutral glycosphingolipids (NGSLs) containing Gal-alpha l -> 6Gal, previously found in the Zygomycetes species Mucor hiemalis, were synthesized. The structures of these compounds are different froth those of other fungal GSLs, and they are expected to be involved in host-parasite interactions. A key step in their synthesis is direct 1,2-cis alpha-selective galactosylation of 4,6-diol tri- and tetrasaccharide acceptors with a galactosyl donor in the presence of N-iodosuccinimide (NIS)/trifluoromethane-sulfonic acid (TfOH). The fully protected glycosides were deprotected to give the two target glycosphingolipids. (C) 2008 Elsevier Ltd. All rights reserved.