N-[(2S,3R,4S,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide | 203571-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4S,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide
• 英文别名: TfaNH(-3d)[Bn(-4)]L-Oli(b)-O-TBDMS；N-[(2S,3R,4S,6R)-6-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3-phenylmethoxyoxan-4-yl]-2,2,2-trifluoroacetamide
• CAS: 203571-10-2
• 化学式: C₂₁H₃₂F₃NO₄Si
• 分子量: 447.57
• InChiKey: CGJGLJFNUUXEIC-OWLYRPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4S,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide 、 [4-((2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-phenyl]-tert-butoxycarbonylamino-acetic acid methyl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(4-{(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-[(2S,4S,5R,6S)-5-benzyloxy-6-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yloxy}-phenyl)-tert-butoxycarbonylamino-acetic acid methyl ester
  参考文献：
  名称：

  A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance

  摘要：

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.

  DOI：

  10.1080/00397919808005074
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 咪唑 、 lithium aluminium tetrahydride 、 sodium azide 、 水 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 73.0h， 生成 N-[(2S,3R,4S,6R)-3-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance

  摘要：

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.

  DOI：

  10.1080/00397919808005074

文献信息

• A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance
  作者：Laurent Daley、Carole Mouton、François Tillequin、Elisabeth Seguin、Jean-Claude Florent、Claude Monneret

  DOI：10.1080/00397919808005074

  日期：1998.1

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.