methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside | 1062111-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside
• CAS: 1062111-60-7
• 化学式: C₄₈H₅₉NO₁₈
• 分子量: 937.992
• InChiKey: BOUWOVPSJSQLNM-WVOPBCFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  225.21
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 、 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4-acetoxy-6-(methoxycarbonyl)-6-(p-tolylthio)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 、 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate(2->6)-methyl 2,3,4-tri-O-benzyl-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

• Solvent Effect in the Synthesis of Sialosyl α(2-6) Galactosides: Is Acetonitrile the only Choice?
  作者：Cristina De Meo、Michael Farris、Nathan Ginder、Bonnie Gulley、Uvege Priyadarshani、Matthew Woods

  DOI：10.1002/ejoc.200800278

  日期：2008.7

  In spite of notable achievements for the synthesis of α-sialosides that have been made in the past decades, sialylation reactions often require low temperatures (–40 to –78 °C) and the use of acetonitrile as a solvent. Herein we report that a C-5 oxazolidinone sialosyl donor gives high yields andstereoselectivities in the presence of dichloromethane and/or tetrahydrofuran at 0 °C. Surprisingly, high

  尽管过去几十年在合成 α-唾液酸苷方面取得了显著成就，但唾液酸化反应通常需要低温（–40 至 –78 °C）并使用乙腈作为溶剂。在本文中，我们报告了 C-5 恶唑烷酮唾液酸供体在二氯甲烷和/或四氢呋喃存在下在 0°C 下具有高产率和立体选择性。令人惊讶的是，即使在环境温度下，在四氢呋喃中也能获得高立体选择性和产率。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）