3,4-O-cyclohexylidene-L-(S)-erythrulose | 229639-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-cyclohexylidene-L-(S)-erythrulose
• 英文别名: L-erythrulose cyclohexylidene acetal；3,4-O-cyclohexylidene-L-erythrulose；1-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]-2-hydroxyethanone
• CAS: 229639-21-8
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: HNJUKKGSTQXWMG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  3,4-O-cyclohexylidene-L-(S)-erythrulose 在 sodium periodate 、 lithium aluminium tetrahydride 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-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
• 作为产物：
  描述：

  L(+)-赤藓酮糖(水合) 、 环己酮 在 camphor-10-sulfonic acid 作用下， 反应 12.0h， 生成 3,4-O-cyclohexylidene-L-(S)-erythrulose
  参考文献：
  名称：

  An Efficient Preparation of Silylated Derivatives of L-Erythrulose 3,4-O-Acetals

  摘要：

  An efficient and reproducible procedure for the preparation of 1-O-silylated derivatives of several 3,4-O-acetals of erythrulose from the parent sugar is described.

  DOI：

  10.1080/00397919908086420

文献信息

• Stereoselective synthesis of (−)-cytoxazone
  作者：Miguel Carda、Florenci González、Richard Sánchez、J.Alberto Marco

  DOI：10.1016/s0957-4166(02)00227-6

  日期：2002.6

  The stereoselective synthesis of the cytokine modulator (−)-cytoxazone in enantiopure form is described. Key steps of the process are a syn-stereoselective aldol addition of a chiral ketone mediated by chlorodicyclohexylborane, and a Curtius rearrangement.

  描述了对映体纯形式的细胞因子调节剂（-）-cytoxazone的立体选择性合成。该方法的关键步骤是由氯二环己基硼烷介导的手性酮的顺式-立体选择性羟醛加成和Curtius重排。
• An Efficient Preparation of Silylated Derivatives of L-Erythrulose 3,4-O-Acetals
  作者：M. Carda、S. Rodriguez、J. Murga、E. Falomir、J. A. Marco、H. Röper

  DOI：10.1080/00397919908086420

  日期：1999.8.1

  An efficient and reproducible procedure for the preparation of 1-O-silylated derivatives of several 3,4-O-acetals of erythrulose from the parent sugar is described.
• 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.