2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside | 904319-27-3

• 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-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside
• 英文别名: Bz(-2)[Mob(-3)][Bn(-6)]Glc(b)-O-EtTMS；[(2R,3R,4S,5R,6R)-5-hydroxy-4-[(4-methoxyphenyl)methoxy]-6-(phenylmethoxymethyl)-2-(2-trimethylsilylethoxy)oxan-3-yl] benzoate
• CAS: 904319-27-3
• 化学式: C₃₃H₄₂O₈Si
• 分子量: 594.777
• InChiKey: SCBQQBBDZYSSNG-FCLIIASSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 碳酸氢钠 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-O-benzoyl-3-O-benzyl-β-D-mannopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)]-2-O-benzoyl-6-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside 、 苯甲酰氯 、 4-甲氧基氯苄 以1.24 g的产率得到2-(trimethylsilyl)ethyl 2-O-benzoyl-6-O-benzyl-3-O-p-methoxybenzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures

  摘要：

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.019

文献信息

• Synthesis of a novel glycosphingolipid from the millipede, Parafontaria laminata armigera, and the assembly of its carbohydrate moiety into multivalent structures
  作者：Noriyasu Hada、Yoshiko Sonoda、Tadahiro Takeda

  DOI：10.1016/j.carres.2006.04.019

  日期：2006.7

  A novel glycosphingolipid, beta-D-Manp-(1 -> 4)-[alpha-L-Fucp-(1 -> 3)]-beta-D-Glcp-(1 -> 1)-Cer, found in the millipede, Parafontaria laminata armigera, and multivalent derivatives of its carbohydrate moiety were synthesized. As the key step, the target glycolipid (1) was obtained through an inversion reaction at the 2-position of a beta-glucopyranoside residue yielding a P-mannopyranoside. In addition, the synthesis of fluorescently labeled trimer and tetramer glycoconjugates (2, 3) was achieved by iterative amide bond formation using a monomer unit (24). (c) 2006 Elsevier Ltd. All rights reserved.