2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester | 858127-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester
• 英文别名: [(2S,3R,4S,5S,6R)-3-methoxycarbonyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trifluoro-N-phenylethanimidate
• CAS: 858127-20-5
• 化学式: C₃₇H₃₆F₃NO₈
• 分子量: 679.69
• InChiKey: DRBXAUMUISMYBB-YODGASFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester 在 5A molecular sieve 、 potassium carbonate 作用下， 以 甲醇 、 环己烷 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 (2R,3R,4R,5S,6R)-2-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-6-[(2S,3R,4S,5S,6R)-2-(4-methoxyphenoxy)-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
  参考文献：
  名称：

  Versatile Use of Ytterbium(III) Triflate and Acid Washed Molecular Sieves in the Activation of Glycosyl Trifluoroacetimidate Donors. Assemblage of a Biologically Relevant Tetrasaccharide Sequence of Globo H

  摘要：

  The nonreducing tetrasaccharide terminus of Globo H has been assembled in good yield and excellent stereocontrol exclusively by using mild and moisture stable agents such as Yb(OTf)(3) and acid washed molecular sieves for the activation of glycosyltrifluoroacetimidate donors in the glycosylation steps.

  DOI：

  10.1021/jo050301x
• 作为产物：
  描述：

  Carbonic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester methyl ester 、 2,2,2-三氟-N-苯基亚氨代乙酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以658 mg的产率得到2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester
  参考文献：
  名称：

  Versatile Use of Ytterbium(III) Triflate and Acid Washed Molecular Sieves in the Activation of Glycosyl Trifluoroacetimidate Donors. Assemblage of a Biologically Relevant Tetrasaccharide Sequence of Globo H

  摘要：

  The nonreducing tetrasaccharide terminus of Globo H has been assembled in good yield and excellent stereocontrol exclusively by using mild and moisture stable agents such as Yb(OTf)(3) and acid washed molecular sieves for the activation of glycosyltrifluoroacetimidate donors in the glycosylation steps.

  DOI：

  10.1021/jo050301x

文献信息

• Versatile Use of Ytterbium(III) Triflate and Acid Washed Molecular Sieves in the Activation of Glycosyl Trifluoroacetimidate Donors. Assemblage of a Biologically Relevant Tetrasaccharide Sequence of Globo H
  作者：Matteo Adinolfi、Alfonso Iadonisi、Alessandra Ravidà、Marialuisa Schiattarella

  DOI：10.1021/jo050301x

  日期：2005.6.1

  The nonreducing tetrasaccharide terminus of Globo H has been assembled in good yield and excellent stereocontrol exclusively by using mild and moisture stable agents such as Yb(OTf)(3) and acid washed molecular sieves for the activation of glycosyltrifluoroacetimidate donors in the glycosylation steps.