TfaNH(-3d)L-Oli4Me(b)-O-TBDMS | 203571-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: TfaNH(-3d)L-Oli4Me(b)-O-TBDMS
• 英文别名: N-[(2S,3R,4S,6R)-6-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• CAS: 203571-09-9
• 化学式: C₁₅H₂₈F₃NO₄Si
• 分子量: 371.472
• InChiKey: ODRBTOPPNPBURW-YFKTTZPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  TfaNH(-3d)L-Oli4Me(b)-O-TBDMS 、 tert-Butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid benzyl 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55%的产率得到tert-Butoxycarbonylamino-{4-[(2S,4S,5R,6S)-5-methoxy-6-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-phenyl}-acetic acid benzyl 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 palladium on activated charcoal 咪唑 、 sodium azide 、 水 、 氢气 、 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 112.5h， 生成 TfaNH(-3d)L-Oli4Me(b)-O-TBDMS
  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.