(4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone | 183506-80-1

• 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: (4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone
• 英文别名: (4R)-4-benzyl-3-[(2R,3S,4S)-3-hydroxy-2,4-dimethyl-5-phenylmethoxypentanoyl]-1,3-oxazolidin-2-one
• CAS: 183506-80-1
• 化学式: C₂₄H₂₉NO₅
• 分子量: 411.498
• InChiKey: ABFFUFMQWMAJAX-KKXYHZGYSA-N

物化性质

• 沸点：
  607.9±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol
  参考文献：
  名称：

  A cross metathesis approach to the synthesis of the C11–C23 fragment of (−)-16-normethyldictyostatin

  摘要：

  The synthesis of the C11-C23 fragment 2 of (-)-16-normethyldictyostatin has been achieved by cross metathesis between two olefinic fragments 4 and 5 followed by a reduction of the double bond at C16-C17. Both the olefinic fragments are easily synthesized in a diastereoselective manner from the common precursor alcohol 7. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.004
• 作为产物：
  描述：

  (R)-3-(benzyloxy)-2-methylpropan-1-ol 在 草酰氯 、 三氟甲磺酸二丁硼 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (4R,2'R,3'S,4'S)-4-benzyl-3-(5'-benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-2-oxazolidinone
  参考文献：
  名称：

  Callipeltin A的合成研究：（2 R，3 R，4 S）-3-羟基-2,4,6-三甲基庚酸的立体选择性合成

  摘要：

  一种有效的且高度立体控制的合成方法是，将被保护的（2 R，3 R，4 S）-3-羟基-2,4,6-三甲基庚酸（β-羟酸单元酰化Callipeltin A的N-末端）进行合成。从（2S）-2-甲基-3-羟基丙酸甲酯开始设计。NMR数据与从卡培特丁A的酸水解产物获得的相应片段的比较表明，应修改上述片段的立体结构。

  DOI：

  10.1016/s0957-4166(02)00178-7

文献信息

• Total synthesis of odoamide, a novel cyclic depsipeptide, from an Okinawan marine cyanobacterium
  作者：Masato Kaneda、Kosuke Sueyoshi、Toshiaki Teruya、Hiroaki Ohno、Nobutaka Fujii、Shinya Oishi

  DOI：10.1039/c6ob01583b

  日期：——

  Odoamide is a novel cyclic depsipeptide with highly potent cytotoxic activity isolated from the Okinawan marine cyanobacterium Okeania sp. It contains a 26-membered macrocycle composed of a fatty acid moiety, a peptide segment and isoleucic acid. Four possible stereoisomers of the odoamide polyketide substructure were synthesised using a chiral pool approach. The first total synthesis of odoamide was

  Odoamide是一种新型的环状二肽，具有从冲绳海洋蓝藻Okeania sp。中分离出来的高效细胞毒活性。它包含一个由脂肪酸部分，肽段和异油酸组成的26元大环。使用手性池方法合成了odoamide聚酮化合物亚结构的四种可能的立体异构体。也成功地完成了对氨基酰胺的第一个全合成。通过比较其核磁共振波谱与天然产物的核磁共振谱，可以验证合成的乙酰胺的结构。
• Synthetic studies on callipeltin A: stereoselective synthesis of (2 R ,3 R ,4 S )-3-hydroxy-2,4,6-trimethylheptanoic acid
  作者：Angela Zampella、Maria Sorgente、Maria Valeria D'Auria

  DOI：10.1016/s0957-4166(02)00178-7

  日期：2002.5

  An efficient and highly stereocontrolled synthesis of protected (2R,3R,4S)-3-hydroxy-2,4,6-trimethylheptanoic acid, the β-hydroxy acid unit that acylates the N-terminus of callipeltin A, has been devised starting from methyl (2S)-2-methyl-3-hydroxypropionate. Comparison of NMR data with the corresponding fragment obtained from the acid hydrolysate of callipeltin A indicates that the stereostructure

  一种有效的且高度立体控制的合成方法是，将被保护的（2 R，3 R，4 S）-3-羟基-2,4,6-三甲基庚酸（β-羟酸单元酰化Callipeltin A的N-末端）进行合成。从（2S）-2-甲基-3-羟基丙酸甲酯开始设计。NMR数据与从卡培特丁A的酸水解产物获得的相应片段的比较表明，应修改上述片段的立体结构。
• Total Synthesis of 10-Deoxymethynolide, the Aglycon of the Macrolide Antibiotic 10-Deoxymethymycin
  作者：Ronaldo A. Pilli、Carlos Kleber Z. de Andrade、Carlos Roberto O. Souto、Armin de Meijere

  DOI：10.1021/jo9809433

  日期：1998.10.1

  A short and efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki-Hiyama-Kishi coupling reaction.
• A cross metathesis approach to the synthesis of the C11–C23 fragment of (−)-16-normethyldictyostatin
  作者：V. Sai Baba、Parthasarathi Das、K. Mukkanti、Javed Iqbal

  DOI：10.1016/j.tetlet.2006.09.004

  日期：2006.11

  The synthesis of the C11-C23 fragment 2 of (-)-16-normethyldictyostatin has been achieved by cross metathesis between two olefinic fragments 4 and 5 followed by a reduction of the double bond at C16-C17. Both the olefinic fragments are easily synthesized in a diastereoselective manner from the common precursor alcohol 7. (c) 2006 Elsevier Ltd. All rights reserved.