Acetic acid (Z)-(4S,5S,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester | 138124-11-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (Z)-(4S,5S,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester
• CAS: 138124-11-5
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: DCKQEOSOAIXZOF-PPCBEUFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (Z)-(4S,5S,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester 在 sodium tetrahydroborate 、 二甲基硫 、 4-甲基苯磺酸吡啶 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 0.34h， 生成 (2S,3S,4R)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036
• 作为产物：
  描述：

  Acetic acid 2-tributylstannanyl-penta-2,3-dienyl ester 在 Lindlar's catalyst 、 magnesium bromide 氢气 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.5h， 生成 Acetic acid (Z)-(4S,5S,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036