(2R,3R,4S)-2-Ethyl-5-methoxymethoxy-4-methyl-pentane-1,3-diol | 135799-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-2-Ethyl-5-methoxymethoxy-4-methyl-pentane-1,3-diol
• 英文别名: (2R,3R,4S)-2-ethyl-5-(methoxymethoxy)-4-methylpentane-1,3-diol
• CAS: 135799-55-2
• 化学式: C₁₀H₂₂O₄
• 分子量: 206.282
• InChiKey: NAHMGDAXDGWXIM-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-Ethyl-5-methoxymethoxy-4-methyl-pentane-1,3-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 (4R,5R)-5-Ethyl-4-((S)-2-methoxymethoxy-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane
  参考文献：
  名称：

  Highly stereoselective SE' additions of .alpha.-alkoxy allylstannanes to chiral aldehydes. Synthesis of a C-1-C-9 subunit of tylonolide

  摘要：

  The racemic alpha-alkoxy allylic stannane RS4 adds to the 2S aldehyde 24 to afford the homoaldol adduct 25 (45%) derived exclusively from the S enantiomer S4 along with isomerized (R)-gamma-alkoxy allylstannane 26 of > 80% ee (50%) and unreacted aldehyde (40%). Use of the nonracemic alpha-alkoxy allylstannane 28 (1:1 mixture of diastereomers) in excess leads to the homoaldol adduct 29, which is transformed in two steps to lactol ether 31, an intermediate in Nicolaou's synthesis of O-micinosyl tylonolide.

  DOI：

  10.1021/jo00019a003
• 作为产物：
  描述：

  (Z,2S,3S,4R)-4-ethyl-1,6-bis(methoxymethoxy)-2-methylhex-5-en-3-ol 在 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 为溶剂， 生成 (2R,3R,4S)-2-Ethyl-5-methoxymethoxy-4-methyl-pentane-1,3-diol
  参考文献：
  名称：

  Highly stereoselective SE' additions of .alpha.-alkoxy allylstannanes to chiral aldehydes. Synthesis of a C-1-C-9 subunit of tylonolide

  摘要：

  The racemic alpha-alkoxy allylic stannane RS4 adds to the 2S aldehyde 24 to afford the homoaldol adduct 25 (45%) derived exclusively from the S enantiomer S4 along with isomerized (R)-gamma-alkoxy allylstannane 26 of > 80% ee (50%) and unreacted aldehyde (40%). Use of the nonracemic alpha-alkoxy allylstannane 28 (1:1 mixture of diastereomers) in excess leads to the homoaldol adduct 29, which is transformed in two steps to lactol ether 31, an intermediate in Nicolaou's synthesis of O-micinosyl tylonolide.

  DOI：

  10.1021/jo00019a003