(2S,4R,5S)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4,6-dimethylheptan-3-one | 308795-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4,6-dimethylheptan-3-one
• 英文别名: (2R,3S)-1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]-3-hydroxy-2,4-dimethylpentan-1-one
• CAS: 308795-20-2
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: GSJVHSMQMNZIND-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4,6-dimethylheptan-3-one 在 2,6-二甲基吡啶 、 氢氟酸 、 高碘酸 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 生成 [2R,3S]-(+)-methyl-3-hydroxy-2,4-dimethyl-pentanoate
  参考文献：
  名称：

  Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

  摘要：

  Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00274-3
• 作为产物：
  描述：

  (S)-cyclohexylidene glyceraldehyde 在 氯代二环己基硼烷 、 sodium acetate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,4R,5S)-1,2-O-cyclohexylidene-1,2,5-trihydroxy-4,6-dimethylheptan-3-one
  参考文献：
  名称：

  Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

  摘要：

  Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00274-3

文献信息

• Stereoselective synthesis of syn-α-methyl-β-hydroxy esters
  作者：Miguel Carda、Juan Murga、Eva Falomir、Florenci González、J.Alberto Marco

  DOI：10.1016/s0957-4166(00)00274-3

  日期：2000.8

  Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.