2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside | 653572-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-6)]Man(b1-4)[Bn(-2)][Mob(-3)][Bn(-6)]Gal(b)-O-EtTMS；(2R,3R,4S,5S,6S)-6-[(2R,3S,4S,5R,6R)-4-[(4-methoxyphenyl)methoxy]-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 653572-86-2
• 化学式: C₆₀H₇₂O₁₂Si
• 分子量: 1013.31
• InChiKey: GDEIPWUHRKJUDG-YIKJIMIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.32
• 重原子数：
  73
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-4,6-O-[(R)-1-(methoxycarbonyl)ethylidene]-1-thio-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以66%的产率得到
  参考文献：
  名称：

  Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside

  摘要：

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.

  DOI：

  10.1081/car-120026456
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 盐酸 、 3 A molecular sieve 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 三乙基硅基三氟甲磺酸酯 、 sodium hydride 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 30.5h， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its Methyl (R)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside

  摘要：

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.

  DOI：

  10.1081/car-120026456

文献信息

• Roy, Samarpita; Sarkar, Sujit Kumar; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 1, p. 137 - 140
  作者：Roy, Samarpita、Sarkar, Sujit Kumar、Roy, Nirmolendu

  DOI：——

  日期：——
• Synthesis of a Blocked Tetrasaccharide Related to the Repeating Unit of the Antigen from <i>Shigella dysenteriae</i> Type 9 in the Form of Its Methyl (<i>R</i>)‐Pyruvate Ester and 2‐(Trimethylsilyl)Ethyl Glycoside
  作者：Samarpita Roy、Nirmolendu Roy

  DOI：10.1081/car-120026456

  日期：2003.12.31

  Starting from D-mannose, D-galactose and D-glucosamine hydrochloride, two disaccharide blocks were synthesized. Schmidt's inverse addition technique of trichloroacetimidate was utilized for the construction of a disaccharide with a beta-mannosidic linkage in good yield. The other disaccharide had a methyl 4,6-(R)pyruvate ester. The two disaccharides in the appropriate form were then allowed to react in the presence of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) to give the desired tetrasaccharide derivative, 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-beta-D-glucopyranosyl-(l --> 3)-2-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-beta-D-galactopyranosyl-(I --> 4)-2,3,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 --> 4)-2,6-di-O-benzyl-3-O-(4-methoxybenzyl)-beta-D-galactopyranoside.