(R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one | 251319-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(E,2R,3S)-3-hydroxy-2-methyl-6-phenylmethoxyhex-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 251319-55-8
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: ULPQHBGYMUDDRJ-XFLDQCBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one 在 titanium(IV) isopropylate 咪唑 、 叔丁基过氧化氢 、 18-冠醚-6 、 4 A molecular sieve 、 三甲基铝 、 二甲羟胺盐酸盐 、 双(三甲基硅烷基)氨基钾 、 LiDBB 、 (-)-diethyl tartrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol
  参考文献：
  名称：

  Asymmetric synthesis of the F-pyran fragment of the altohyrtins

  摘要：

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01481-1
• 作为产物：
  描述：

  烯丙基苄基醚 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one
  参考文献：
  名称：

  Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

  摘要：

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.080

文献信息

• Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.tet.2011.01.080

  日期：2011.3

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of the F-pyran fragment of the altohyrtins
  作者：James C. Anderson、Benjamin P. McDermott

  DOI：10.1016/s0040-4039(99)01481-1

  日期：1999.9

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.