phenyl 2-O-acetyl-6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside | 653572-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-acetyl-6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside
• 英文别名: TBDPS(-6)Gal2Ac(b)-SPh；[(2S,3R,4S,5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4,5-dihydroxy-2-phenylsulfanyloxan-3-yl] acetate
• CAS: 653572-75-9
• 化学式: C₃₀H₃₆O₆SSi
• 分子量: 552.764
• InChiKey: PYQPRRLEKKYGKQ-LLQHYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-acetyl-6-O-(tert-butyl(diphenyl)silyl)-1-thio-β-D-galactopyranoside 在 吡啶 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 四丁基氟化铵 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 、 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 正丁醇 为溶剂， 反应 48.5h， 生成 phenyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl(1->3)-2-O-benzoyl-1-thio-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
• 作为产物：
  描述：

  phenyl 6-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 4.0h， 生成 phenyl 2-O-acetyl-6-O-(tert-butyl(diphenyl)silyl)-1-thio-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