methyl (5S,6S,7R,3E)-7,8-(isopropylidenedioxy)-5-hydroxy-6-(1-tetrahydropyranyloxy)-3-octenoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (5S,6S,7R,3E)-7,8-(isopropylidenedioxy)-5-hydroxy-6-(1-tetrahydropyranyloxy)-3-octenoate
• 英文别名: methyl (E,5R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-hydroxy-6-(oxan-2-yloxy)hex-3-enoate
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: XLEFUTGCONJKQT-XDZBUKDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (5S,6S,7R,3E)-7,8-(isopropylidenedioxy)-5-hydroxy-6-(1-tetrahydropyranyloxy)-3-octenoate 以100%的产率得到
  参考文献：
  名称：

  Pak Chwang Siek, Lee Eun, Lee Ge Hyeong, J. Org. Chem, 58 (1993) N 6, S 1523-1530

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-{(4R,5R)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(tetrahydro-pyran-2-yloxy)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid methyl ester 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到methyl (5S,6S,7R,3E)-7,8-(isopropylidenedioxy)-5-hydroxy-6-(1-tetrahydropyranyloxy)-3-octenoate
  参考文献：
  名称：

  Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol

  摘要：

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.

  DOI：

  10.1021/jo00058a038

文献信息

• Pak Chwang Siek, Lee Eun, Lee Ge Hyeong, J. Org. Chem, 58 (1993) N 6, S 1523-1530
  作者：Pak Chwang Siek, Lee Eun, Lee Ge Hyeong

  DOI：——

  日期：——
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.