[(2S,3R,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-yl] acetate | 203571-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-yl] acetate
• CAS: 203571-04-4
• 化学式: C₁₄H₂₇N₃O₄Si
• 分子量: 329.472
• InChiKey: HFLXKNUWIDDBQF-TYAGLYMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3R,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-yl] acetate 在 palladium on activated charcoal 氢气 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 62.0h， 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
• 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 作用下， 以 二氯甲烷 为溶剂， 反应 50.5h， 生成 [(2S,3R,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-yl] acetate
  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 efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone
  作者：Bernd Renneberg、Yue-Ming Li、Hartmut Laatsch、Heinz-Herbert Fiebig

  DOI：10.1016/s0008-6215(00)00257-3

  日期：2000.12

  constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-e

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。
• Grynkiewicz; Fokt; Skibicki, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 335 - 347
  作者：Grynkiewicz、Fokt、Skibicki、Przewloka、Szeja、Priebe

  DOI：——

  日期：——