methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-4-O-tert-butyldimethylsilyl-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranoside | 1356459-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-4-O-tert-butyldimethylsilyl-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: methyl (2R,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-2-[[(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]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 1356459-55-6
• 化学式: C₃₆H₅₉NO₁₇Si
• 分子量: 805.946
• InChiKey: BKUDIKAQDSWMFM-VICQIGFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  methyl [p-methylphenyl 5-acetamido-8,9-O-isopropylidene-3,5-dideoxy-4-O-tert-butyldimethylsilyl-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside]onate 在 水 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 32.5h， 生成 methyl 5-acetamido-7,8,9-tri-O-acetyl-3,5-dideoxy-4-O-tert-butyldimethylsilyl-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  How O-Substitution of Sialyl Donors Affects Their Stereoselectivity

  摘要：

  The profound effect of substituents at C-5 of glycosyl sialosides on their stereoselectivity is well-known although the exact nature of this effect is somewhat less understood. Presented herein is a comparative study of a range of novel sialyl donors with various O-substituents. It is demonstrated that O-substituents at C-4 and C-7 may also have a significant effect on the reactivity of sialyl donors and on the stereoselectivity of chemical sialylation.

  DOI：

  10.1021/ol3000475

文献信息

• Sialylations reactions: Expanding the effect of silicon protecting groups at C-4
  作者：Alexanndra Behm、Jessica Hafner、Natalie Goeckner、Matthew Lohman、Cristina De Meo

  DOI：10.1016/j.carres.2022.108707

  日期：2022.12

  goal into evaluating the effect of O-protecting groups in sialylation reactions, we compared the reactivities of phenylthio α- and β-sialyl donors protected at C-4 with tert-butyldimethyl silyl (TBDMS) and tri-isopropylsilyl (TIPS) groups in the coupling with primary and secondary galactosyl acceptors. The effect of the solvent and the donor's anomeric configuration were investigated and compared to

  作为评估O保护基团在唾液酸化反应中的影响的一般研究目标的一部分，我们比较了在 C-4 处保护的苯硫基 α- 和 β- 唾液酸供体与叔丁基二甲基甲硅烷基 (TBDMS) 和三-与初级和次级半乳糖基受体偶联的异丙基甲硅烷基 (TIPS) 基团。研究了溶剂和供体异头构型的影响，并与之前公布的数据进行了比较。事实证明，C-4 上的硅基团对唾液酸化反应有重大影响，一般而言，使用乙腈可以优化它们的整体性能。