(4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-5-phenyloxazolidin-2-one | 218766-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-5-phenyloxazolidin-2-one
• 英文别名: (4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenyl-1,3-oxazolidin-2-one
• CAS: 218766-12-2
• 化学式: C₁₆H₂₅NO₃Si
• 分子量: 307.465
• InChiKey: UEABAMGRGAEUGT-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-5-phenyloxazolidin-2-one 在 吡啶 、 氢氧化钾 、 氢氟酸 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 55.25h， 生成 (1R,2R)-2-amino-3-(N-morpholino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j
• 作为产物：
  描述：

  tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 在 titanium(IV) isopropylate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 生成 (4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  总合成具有有趣的抗结核和抗疟疾活性的海洋环肽A，C和D †

  摘要：

  环豆素是含有四个不同氨基酸的环状七肽。已经开发出用于其合成的新的合成方案，从而导致了三种天然存在的环烷的合成和生物学评估。有趣的是，水手素针对两个完全不同的靶标：Clp C1，结核分枝杆菌（MTB）的酪蛋白水解蛋白酶的亚基，以及恶性疟原虫的PfAp 3 Ase 。因此，对于开发抗结核和疟疾药物而言，水手素是有趣的先导结构。

  DOI：

  10.1039/c6ob00800c

文献信息

• Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities
  作者：Philipp Barbie、Uli Kazmaier

  DOI：10.1039/c6ob00800c

  日期：——

  Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase

  环豆素是含有四个不同氨基酸的环状七肽。已经开发出用于其合成的新的合成方案，从而导致了三种天然存在的环烷的合成和生物学评估。有趣的是，水手素针对两个完全不同的靶标：Clp C1，结核分枝杆菌（MTB）的酪蛋白水解蛋白酶的亚基，以及恶性疟原虫的PfAp 3 Ase 。因此，对于开发抗结核和疟疾药物而言，水手素是有趣的先导结构。
• Glycosyltransferase Inhibitors:  Synthesis of <scp>d</scp>-<i>threo</i>-PDMP, <scp>l</scp>-<i>threo</i>-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from <scp>d</scp>- or <scp>l</scp>-Serine
  作者：Scott A. Mitchell、Bryan D. Oates、Hossein Razavi、Robin Polt

  DOI：10.1021/jo980951j

  日期：1998.11.1

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.