5-Se-Benzyl-1,2-O-isopropyliden-5-seleno-α-D-xylofuranose | 16885-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Se-Benzyl-1,2-O-isopropyliden-5-seleno-α-D-xylofuranose
• 英文别名: (3aR,5S,6R,6aR)-5-(benzylselanylmethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol；(3aR,5S,6R,6aR)-5-(benzylselanylmethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 16885-58-8
• 化学式: C₁₅H₂₀O₄Se
• 分子量: 343.281
• InChiKey: KAWXZOLULKOLFU-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Se-Benzyl-1,2-O-isopropyliden-5-seleno-α-D-xylofuranose 、 乙硫醇 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 生成 (2R,3R,4S)-5-Benzylselanyl-1,1-bis-ethylsulfanyl-pentane-2,3,4-triol
  参考文献：
  名称：

  Selenium derivatives of L-arabinose, D-ribose, and D-xylose

  摘要：

  DOI：

  10.1016/s0008-6215(00)83177-8
• 作为产物：
  描述：

  二苄基二硒醚 、 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.17h， 以72%的产率得到5-Se-Benzyl-1,2-O-isopropyliden-5-seleno-α-D-xylofuranose
  参考文献：
  名称：

  Synthesis of 5′-seleno-xylofuranosides

  摘要：

  The synthesis of selenium derivatives of naturally occurring chiral molecules is becoming increasingly important in recent years. In this context, we describe herein an easy, straightforward synthetic route for the preparation of a series of chiral seleno-furanosides, starting from the readily available carbohydrate D-xylose. In addition, selected compounds were screened as inhibitors of the delta-aminolevulinate dehyclratase (delta-ALA-D) enzyme. Diselenide 4 was found to reduce significantly the enzymatic activity, while seleno-furanoside la increased delta-ALA-D activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.033

文献信息

• Selenium derivatives of L-arabinose, D-ribose, and D-xylose
  作者：Karl Blumberg、Anthony Fuccello、Theodorus van Es

  DOI：10.1016/s0008-6215(00)83177-8

  日期：1977.12
• Synthesis of 5′-seleno-xylofuranosides
  作者：Hugo C. Braga、Hélio A. Stefani、Márcio W. Paixão、Francielli W. Santos、Diogo S. Lüdtke

  DOI：10.1016/j.tet.2010.03.033

  日期：2010.5

  The synthesis of selenium derivatives of naturally occurring chiral molecules is becoming increasingly important in recent years. In this context, we describe herein an easy, straightforward synthetic route for the preparation of a series of chiral seleno-furanosides, starting from the readily available carbohydrate D-xylose. In addition, selected compounds were screened as inhibitors of the delta-aminolevulinate dehyclratase (delta-ALA-D) enzyme. Diselenide 4 was found to reduce significantly the enzymatic activity, while seleno-furanoside la increased delta-ALA-D activity. (C) 2010 Elsevier Ltd. All rights reserved.