(2S,3R,4S,6S)-N,N,2-trimethyl-6-phenylsulfanyl-4-triethylsilyloxyoxan-3-amine | 675607-74-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S,3R,4S,6S)-N,N,2-trimethyl-6-phenylsulfanyl-4-triethylsilyloxyoxan-3-amine
• CAS: 675607-74-6
• 化学式: C₂₀H₃₅NO₂SSi
• 分子量: 381.655
• InChiKey: NAUNNUCBGMKUQC-FRYIKTPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-3-戊醇 、 (2S,3R,4S,6S)-N,N,2-trimethyl-6-phenylsulfanyl-4-triethylsilyloxyoxan-3-amine 在 2,6-二叔丁基-4-甲基吡啶 、 六氟磷酸银 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3R,4S,6R)-6-(2,4-dimethylpentan-3-yloxy)-N,N,2-trimethyl-4-triethylsilyloxyoxan-3-amine
  参考文献：
  名称：

  A Direct and Efficientα-Selective Glycosylation Protocol for the Kedarcidin Sugar,L-Mycarose: AgPF6 as a Remarkable Activator of 2-Deoxythioglycosides

  摘要：

  The α-selective effect and potency of AgPF6 on readily prepared 2-deoxythioglycosides allows the direct attachment of a partially protected allo-sugar, such as L-mycarose, to an advanced and hindered aglycon unit of kedarcidin. This method also permits access to other 2-deoxyglycosides in an expedient and mild manner. PMBM=p-methoxybenzyloxymethyl, Alloc=allyloxycarbonyl, TES=triethylsilyl.

  DOI：

  10.1002/1521-3773(20010302)40:5<946::aid-anie946>3.0.co;2-g
• 作为产物：
  描述：

  三乙基氯硅烷 在 咪唑 、 四丁基碘化铵 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (2S,3R,4S,6S)-N,N,2-trimethyl-6-phenylsulfanyl-4-triethylsilyloxyoxan-3-amine
  参考文献：
  名称：

  Use of Polystyrene-Supported DBU in the Synthesis and α-Selective Glycosylation Study of the Unstable Schmidt Donor of l-Kedarosamine

  摘要：

  In the alpha-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-alpha-glycoside of the ansamacrolicle substructure of the kedarcidin chromophore.

  DOI：

  10.1021/ol036353v

文献信息

• A Direct and Efficientα-Selective Glycosylation Protocol for the Kedarcidin Sugar,L-Mycarose: AgPF6 as a Remarkable Activator of 2-Deoxythioglycosides
  作者：Martin J. Lear、Fumihiko Yoshimura、Masahiro Hirama

  DOI：10.1002/1521-3773(20010302)40:5<946::aid-anie946>3.0.co;2-g

  日期：2001.3.2

  The α-selective effect and potency of AgPF6 on readily prepared 2-deoxythioglycosides allows the direct attachment of a partially protected allo-sugar, such as L-mycarose, to an advanced and hindered aglycon unit of kedarcidin. This method also permits access to other 2-deoxyglycosides in an expedient and mild manner. PMBM=p-methoxybenzyloxymethyl, Alloc=allyloxycarbonyl, TES=triethylsilyl.
• Use of Polystyrene-Supported DBU in the Synthesis and α-Selective Glycosylation Study of the Unstable Schmidt Donor of <scp>l</scp>-Kedarosamine
  作者：Isao Ohashi、Martin J. Lear、Fumihiko Yoshimura、Masahiro Hirama

  DOI：10.1021/ol036353v

  日期：2004.3.1

  In the alpha-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-alpha-glycoside of the ansamacrolicle substructure of the kedarcidin chromophore.