3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: [(4aR,6S,7S,8R,8aR)-2,2-ditert-butyl-8-[tert-butyl(dimethyl)silyl]oxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-7-yl] 2,2-dimethylpropanoate
• 化学式: C₃₇H₆₈O₁₂Si₂
• 分子量: 761.111
• InChiKey: NFCFZLMMSZZHPI-JGSXYHKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  benzyl 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-α-D-mannopyranoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氢气 、 甲苯 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 22.5h， 生成 3-O-tert-butyldimethylsilyl-4,6-di-O-(tert-butyl)silanediyl-2-O-pivaloyl-α-D-mannopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Formation of β-Glucosamine and β-Mannose Linkages Using Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta -Glucosamine glycosides were formed preferentially and in good yield. beta -Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.

  DOI：

  10.1021/ol006566+

文献信息

• Formation of β-Glucosamine and β-Mannose Linkages Using Glycosyl Phosphates
  作者：Obadiah J. Plante、Emma R. Palmacci、Peter H. Seeberger

  DOI：10.1021/ol006566+

  日期：2000.11.1

  [GRAPHICS]Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta -Glucosamine glycosides were formed preferentially and in good yield. beta -Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.