(3R,4S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester | 149083-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester
• CAS: 149083-16-9
• 化学式: C₂₁H₂₈O₆S
• 分子量: 408.516
• InChiKey: BMTVWXWAIFHIRE-NOCIGQNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester 在 水 、 二异丁基氢化铝 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 生成 [(R)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-hydroxy-tetrahydro-pyran-4-yl]-acetaldehyde
  参考文献：
  名称：

  Synthetic studies on the rhizoxins. 1. Two stereoselective routes to a functionalized C(1)-C(9) subunit

  摘要：

  Two syntheses of a potential C1-C-9 subunit of rhizoxin are described. In the first, chelation-controlled allylstannane addition to optically pure aldehyde 3, conversion to unsaturated ester 7, and stereoselective intramolecular Michael addition is used to establish the relative stereochemistry at C-7 and C-8 (rhizoxin numbering). In the second, an Evans aldol condensation is used to control absolute and relative stereochemistry at these centers. Both approaches use thermodynamic control to establish the correct stereochemistry at C5.

  DOI：

  10.1021/jo00067a003
• 作为产物：
  描述：

  3-O-[(E,2R,3R)-7-ethylsulfanyl-2-methyl-7-oxo-1-phenylmethoxyhept-5-en-3-yl] 1-O-methyl propanedioate 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 (3R,4S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester 、 (3S,4R,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-4-ethylsulfanylcarbonylmethyl-2-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies on the rhizoxins. 1. Two stereoselective routes to a functionalized C(1)-C(9) subunit

  摘要：

  Two syntheses of a potential C1-C-9 subunit of rhizoxin are described. In the first, chelation-controlled allylstannane addition to optically pure aldehyde 3, conversion to unsaturated ester 7, and stereoselective intramolecular Michael addition is used to establish the relative stereochemistry at C-7 and C-8 (rhizoxin numbering). In the second, an Evans aldol condensation is used to control absolute and relative stereochemistry at these centers. Both approaches use thermodynamic control to establish the correct stereochemistry at C5.

  DOI：

  10.1021/jo00067a003