((2R,4S,5R,6S)-4-Azido-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane | 203571-08-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,4S,5R,6S)-4-Azido-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane
• 英文别名: [(2R,4S,5R,6S)-4-azido-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 203571-08-8
• 化学式: C₁₉H₃₁N₃O₃Si
• 分子量: 377.559
• InChiKey: HMCGDCPMLKXEMB-OWLYRPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((2R,4S,5R,6S)-4-Azido-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane 在 lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (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 、 sodium azide 、 水 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 ((2R,4S,5R,6S)-4-Azido-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tert-butyl-dimethyl-silane
  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.