1,3-benzylidene-D-erythritol | 347362-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1,3-benzylidene-D-erythritol
• 英文别名: 1,3-O-Benzyliden-L-erythritol；(2S,4R,5S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol
• CAS: 347362-36-1
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: GUOMTMWCUMBRFX-AXFHLTTASA-N

物化性质

• 沸点：
  403.6±40.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1,3-benzylidene-D-erythritol 、 二苄基磷酰基氯 在 吡啶 作用下， 以 苯 为溶剂， 反应 96.0h， 生成 1,3-O-benzylidene-D-erythritol 4-dibenzylphosphate
  参考文献：
  名称：

  Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from Agrobacterium tumefaciens

  摘要：

  The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where it intersects with the mevalonate pathway found in some Bacteria, Archaea, and Eukarya, including the cytosol of plants. D-3-Methylerythritol-4-phosphate (MEP), the first pathway-specific intermediate in the pathway, is converted to IPP and DMAPP by the consecutive action of the IspD-H proteins. We synthesized five D-MEP analogues-D-erythritol-4-phosphate (EP), D-3-methylthrietol-4-phosphate (MTP), D-3-ethylerythritol-4-phosphate (EEP), D-1-amino-3-methylerythritol-4-phosphate (NMEP), and D-3-methylerythritol-4-thiolophosphate (MESP)-and studied their ability to function as alternative substrates for the reactions catalyzed by the IspDF fusion and IspE proteins from Agrobacterium tumefaciens, which covert MEP to the corresponding eight-membered cyclic diphosphate. All of the analogues, except MTP, and their products were substrates for the three consecutive enzymes.

  DOI：

  10.1021/jo501529k
• 作为产物：
  描述：

  2,4-O-benzylidene-D-threose 在 ruthenium(IV) oxide 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 四丁基氟化铵 、 苄基三乙基氯化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.17h， 生成 1,3-benzylidene-D-erythritol
  参考文献：
  名称：

  Synthesis of Enantiopure 2-C-Methyl-d-erythritol 4-Phosphate and 2,4-Cyclodiphosphate from d-Arabitol

  摘要：

  Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from D-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.

  DOI：

  10.1021/ol0362562

文献信息

• Synthesis of Enantiopure 2-<i>C</i>-Methyl-<scp>d</scp>-erythritol 4-Phosphate and 2,4-Cyclodiphosphate from <scp>d</scp>-Arabitol
  作者：Marek Urbansky、Chad E. Davis、Jacob D. Surjan、Robert M. Coates

  DOI：10.1021/ol0362562

  日期：2004.1.1

  Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from D-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.
• Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from <i>Agrobacterium tumefaciens</i>
  作者：Sergiy G. Krasutsky、Marek Urbansky、Chad E. Davis、Christian Lherbet、Robert M. Coates、C. Dale Poulter

  DOI：10.1021/jo501529k

  日期：2014.10.3

  The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where it intersects with the mevalonate pathway found in some Bacteria, Archaea, and Eukarya, including the cytosol of plants. D-3-Methylerythritol-4-phosphate (MEP), the first pathway-specific intermediate in the pathway, is converted to IPP and DMAPP by the consecutive action of the IspD-H proteins. We synthesized five D-MEP analogues-D-erythritol-4-phosphate (EP), D-3-methylthrietol-4-phosphate (MTP), D-3-ethylerythritol-4-phosphate (EEP), D-1-amino-3-methylerythritol-4-phosphate (NMEP), and D-3-methylerythritol-4-thiolophosphate (MESP)-and studied their ability to function as alternative substrates for the reactions catalyzed by the IspDF fusion and IspE proteins from Agrobacterium tumefaciens, which covert MEP to the corresponding eight-membered cyclic diphosphate. All of the analogues, except MTP, and their products were substrates for the three consecutive enzymes.