3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose | 131566-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
• 英文别名: 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-D-ribofuranoside；(3aR,5R,6R,6aR)-2,2,5-trimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 131566-84-2
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: ZDMPUJVEPHATGJ-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 在 碘 作用下， 反应 1.5h， 以92%的产率得到
  参考文献：
  名称：

  通过连续的克莱森重排-分子内酯烯酸酯烷基化合成（-）-reiswigin

  摘要：

  （-）-Reiswigin A（1），一种新型的抗病毒二萜，已经通过使用顺序Claisen重排-分子内酯烯醇化烷基化策略以高度立体选择性的方式合成。

  DOI：

  10.1016/0040-4039(94)80021-9
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose 在 吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.5h， 生成 3-O-Benzyl-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose
  参考文献：
  名称：

  Study of 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues

  摘要：

  1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.

  DOI：

  10.1021/ol048459b

文献信息

• A total synthesis of (−)-reiswigin a via sequential claisen rearrangement-intramolecular ester enolate alkylation
  作者：Deukjoon Kim、Kye Jung Shin、Ik Yoen Kim、Sang Woo Park

  DOI：10.1016/0040-4039(94)80021-9

  日期：1994.10

  (−)-Reiswigin A (1), a novel anti-viral diterpene, has been synthesized in a highly stereoselective manner utilizing a sequential Claisen rearrangement — intramolecular ester enolate alkylation strategy.

  （-）-Reiswigin A（1），一种新型的抗病毒二萜，已经通过使用顺序Claisen重排-分子内酯烯醇化烷基化策略以高度立体选择性的方式合成。
• Metal-graphite reagents in carbohydrate chemistry. 8. The scope and limitations of the use of zinc/silver-graphite in the synthesis of carbohydrate-derived substituted hex-5-enals and pent-4-enals
  作者：Alois Fuerstner、Denis Jumbam、Judith Teslic、Hans Weidmann

  DOI：10.1021/jo00006a047

  日期：1991.3
• FURSTNER, ALOIS;JUMBAM, DENIS;TESLIC, JUDITH;WEIDMANN, HANS, J. ORG. CHEM., 56,(1991) N, C. 2213-2217
  作者：FURSTNER, ALOIS、JUMBAM, DENIS、TESLIC, JUDITH、WEIDMANN, HANS

  DOI：——

  日期：——
• Study of 1-Deoxy-<scp>d</scp>-xylulose-5-phosphate Reductoisomerase:  Synthesis and Evaluation of Fluorinated Substrate Analogues
  作者：Alexander Wong、Jeffrey W. Munos、Vidusha Devasthali、Kenneth A. Johnson、Hung-wen Liu

  DOI：10.1021/ol048459b

  日期：2004.9.1

  1-Deoxy-D-xylulose-5-phosphate (DXP) reductoisomerase is a NADPH-dependent enzyme catalyzing the conversion of DXP to methyl-D-erythritol 4-phosphate (MEP). In this study, each of the hydroxyl groups in DXP and one of its C-1 hydrogen atoms, were separately replaced with a fluorine atom and the effect of the substitution on the catalytic turnover was examined. It was found that the 1-fluoro-DXP is a poor substrate, while both 3- and 4-fluoro-DXP behave as noncompetitive inhibitors.