(2R,3R,4S)-1-(Benzyloxy)-2,4-dimethyl-5-octyn-3-ol | 138124-47-7

• 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: (2R,3R,4S)-1-(Benzyloxy)-2,4-dimethyl-5-octyn-3-ol
• 英文别名: (2R,3R,4S)-2,4-dimethyl-1-phenylmethoxyoct-5-yn-3-ol
• CAS: 138124-47-7
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: GVJYHKXLNZJWOY-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-1-(Benzyloxy)-2,4-dimethyl-5-octyn-3-ol 在 Lindlar's catalyst 二甲基硫 、 氢气 、 臭氧 作用下， 以 苯 为溶剂， 反应 1.17h， 生成 (2R,3S,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanal
  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：

  (R)-3-benzyloxy-2-methylpropanal 、 3-(tributylstannyl)-3,4-hexadiene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.1h， 生成 (2R,3R,4S)-1-(Benzyloxy)-2,4-dimethyl-5-octyn-3-ol 、 (2R,3S,4R)-1-Benzyloxy-2,4-dimethyl-oct-5-yn-3-ol
  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

文献信息

• Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents
  作者：James A. Marshall、Jolyon F. Perkins、Mark A. Wolf

  DOI：10.1021/jo00122a041

  日期：1995.9

  The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3 . OEt(2) promotion), syn,anti (MgBr2 . OEt(2) promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.