(R)-4-benzyl-3-((2R,3R,4S)-3-hydroxy-4-methoxy-2,6-dimethylheptanoyl)oxazolidin-2-one | 912653-96-4

• 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: (R)-4-benzyl-3-((2R,3R,4S)-3-hydroxy-4-methoxy-2,6-dimethylheptanoyl)oxazolidin-2-one
• CAS: 912653-96-4
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: ZDGCXRRZNAFFCX-NRSFXHEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-((2R,3R,4S)-3-hydroxy-4-methoxy-2,6-dimethylheptanoyl)oxazolidin-2-one 在 sodium tetrahydroborate 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 (2R,4R,5S)-4-((S)-1-methoxy-3-methylbutyl)-5-methyl-2-phenyl-[1,3]dioxane
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056
• 作为产物：
  描述：

  (S)-2-methoxy-4-methylpentanoic acid methyl ester 在 sodium hypochlorite 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium aluminium tetrahydride 、 三氟甲磺酸二丁硼 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 potassium bromide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 5.75h， 生成 (R)-4-benzyl-3-((2R,3R,4S)-3-hydroxy-4-methoxy-2,6-dimethylheptanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective allyl transfer to chiral α-methoxycarbaldehydes: A model study related to the C-9/C-15 fragment of geldanamycin

  摘要：

  The enantiomerically pure alpha-methoxycarbaldehyde 3 was prepared from L-leucine in five steps and 31% overall yield. The aldehyde was subjected to a diastereoselective BF3-mediated crotylation with silane 4 and to various reagent-controlled addition reactions. The configuration of aldol addition products 19 and 20 was proven by single crystal X-ray crystallography. Based on these data spectral comparison allowed an unambiguous assignment of the desired anti,syn-crotylation product 2b and of the syn,syn-crotylation product 2a. Unexpectedly, product 2a of the BF3-mediated crotylation is formally the product of chelation-control. The anti, syn-crotylation product 2b, which is a model for the C-9/C-15 fragment of geldanamycin, was obtained by a reagent-controlled crotylation with the chiral (Z)-crotylborane 23. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.056