(4R,5S)-3-benzyl-5-((1S)-2-tert-butyldiphenylsilyloxy-1-hydroxyethyl)-4-vinyl-1,3-oxazolan-2-one | 357278-39-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R,5S)-3-benzyl-5-((1S)-2-tert-butyldiphenylsilyloxy-1-hydroxyethyl)-4-vinyl-1,3-oxazolan-2-one
• 英文别名: (4R,5S)-3-benzyl-5-[(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-4-ethenyl-1,3-oxazolidin-2-one
• CAS: 357278-39-8
• 化学式: C₃₀H₃₅NO₄Si
• 分子量: 501.698
• InChiKey: YAOAYZFLJMUVPO-PKTNWEFCSA-N

物化性质

• 沸点：
  625.8±55.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-benzyl-5-((1S)-2-tert-butyldiphenylsilyloxy-1-hydroxyethyl)-4-vinyl-1,3-oxazolan-2-one 在 四丁基氟化铵 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以85%的产率得到(4R,5S)-3-Benzyl-5-((S)-1,2-dihydroxy-ethyl)-4-vinyl-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern

  摘要：

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

  DOI：

  10.1021/jo048766v
• 作为产物：
  描述：

  (2R,3R)-4-(tert-Butyldiphenylsilyloxy)-2,3-epoxybutan-1-al 在 吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 、 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (4R,5S)-3-benzyl-5-((1S)-2-tert-butyldiphenylsilyloxy-1-hydroxyethyl)-4-vinyl-1,3-oxazolan-2-one
  参考文献：
  名称：

  A New Access to Polyhydroxylated Pyrrolidines from Epoxyaldehydes

  摘要：

  我们的方法依赖于从相应的醛中衍生出的手性δ±,δ²-环氧亚胺的立体控制乙烯基化。用碳酸阴离子对环氧乙烷进行区域选择性开环，可形成恶唑烷酮中间体，并由此合成出葡萄糖苷酶抑制剂 1,4-二脱氧-1,4-亚氨基-d-葡萄糖醇 (14)。直接环化成 2-乙烯基-3,4-环氧吡咯烷后，就得到了制备合成氮杂糖类似物的重要中间体。

  DOI：

  10.1055/s-2001-14593

文献信息

• New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon
  作者：Magalie Collet、Yves Génisson、Michel Baltas

  DOI：10.1016/j.tetasy.2007.06.002

  日期：2007.6

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.
• Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern
  作者：Tahar Ayad、Vanessa Faugeroux、Yves Génisson、Chantal André,、Michel Baltas、Liliane Gorrichon

  DOI：10.1021/jo048766v

  日期：2004.12.1

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.
• A New Access to Polyhydroxylated Pyrrolidines from Epoxyaldehydes
  作者：Tahar Ayad、Yves Génisson、Michel Baltas、Liliane Gorrichon

  DOI：10.1055/s-2001-14593

  日期：——

  Our approach relies on the stereocontrolled vinylation of a chiral α,β-epoxyimine derived from the corresponding aldehyde. Regioselective opening of the oxirane with carbonate anion allowed the formation of an oxazolidinone intermediate from which the glucosidase inhibitor 1,4-dideoxy-1,4-imino-d-glucitol (14) was synthesised. Direct cyclisation into a 2-vinyl-3,4-epoxypyrrolidine afforded a valuable intermediate for the preparation of synthetic azasugar analogues.

  我们的方法依赖于从相应的醛中衍生出的手性δ±,δ²-环氧亚胺的立体控制乙烯基化。用碳酸阴离子对环氧乙烷进行区域选择性开环，可形成恶唑烷酮中间体，并由此合成出葡萄糖苷酶抑制剂 1,4-二脱氧-1,4-亚氨基-d-葡萄糖醇 (14)。直接环化成 2-乙烯基-3,4-环氧吡咯烷后，就得到了制备合成氮杂糖类似物的重要中间体。