1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose | 245441-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose
• 英文别名: 1,2-O-Isopropyliden-5-C-phenyl-α-D-gluco-pentofuranose；1,2-O-Isopropyliden-5-C-phenyl-β-L-ido-pentofuranose；(3aR,5R,6S,6aR)-5-[hydroxy(phenyl)methyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 245441-87-6
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: RLPUQJHWOKMKBL-ONQCXXIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose 在 偶氮二异丁腈 、 Celite 、 硫酸 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 14.0h， 生成 (+)-harzialactone A
  参考文献：
  名称：

  A concise synthesis of harzialactone A from d-glucose and revision of absolute stereochemistry

  摘要：

  Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00245-1
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium periodate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1,2-O-isopropylidene-5-C-phenyl-β-L-ido/α-D-gluco-pentofuranose
  参考文献：
  名称：

  A concise synthesis of harzialactone A from d-glucose and revision of absolute stereochemistry

  摘要：

  Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00245-1

文献信息

• Tetramethylethylenediammonium Bichromate (TMEDADC): A New Selective Oxidation Reagent
  作者：S. Chandrasekhar、Mohamed Takhi、Suchismita Mohapatra

  DOI：10.1080/00397919608003816

  日期：1996.11

  Abstract TMEDADC obtained from Chromium trioxide and TMEDA has been conveniently utilized for the selective oxidation of benzylic and allylic alcohols in excellent yield for the first time.

  摘要 从三氧化铬和 TMEDA 中获得的 TMEDADC 首次以优异的收率方便地用于苯甲醇和烯丙醇的选择性氧化。
• Synthesis of Natural and Unnatural Enantiomers of Goniofufurone and Its 7-Epimers from D-Glucose. Application of Palladium(II) - Catalyzed Oxycarbonylation of Unsaturated Polyols
  作者：Tibor Gracza、Volker Jäger

  DOI：10.1055/s-1994-25694

  日期：——

  Syntheses of 3,6-anhydro-2-deoxy-7-phenylglyconolactones (+)-1 and (+)-2 with D- and L-glycero-D-ido configuration, respectively, as well as of their enantiomers (-)-1 and (-)-2, from D-glucose are presented. The key steps are, (i) phenylmagnesium bromide additions to C1 or C5 of glucose-derived aldehydes 7 and 10, respectively, and (ii), palladium (II)-catalyzed oxycarbonylation of intermediate 1-phenyl-D- and -L-5-hexenitols 8/9 or 14/15. The syntheses proceed in 7 steps with 6% and 18% over-all yield for (+)-1/ (+)-2, and in 6 steps/ 11% and 16% for (-)-1/ (-)-2 ( from monoacetone glucose). The absolute configurations of goniofufurone (+)-1 and its 7-epimer (+)-2 thus established are in accord with those of all suggested biogenetic precursors and allowed, e.g., to propose the absolute configuration of (+)-goniopypyrone, a related cytotoxic, bicyclic styryllactone, and structures of potential biosynthetic intermediates not identified so far.

  分别具有 D- 和 L-甘油-D-ido 构型的 3,6-脱水-2-脱氧-7-苯基乙醇内酯 (+)-1 和 (+)-2 及其对映体 (-) 的合成呈现了来自D-葡萄糖的-1和(-)-2。关键步骤是，(i) 苯基溴化镁分别加成到葡萄糖衍生的醛 7 和 10 的 C1 或 C5 上，以及 (ii) 钯 (II) 催化的中间体 1-苯基-D- 和 -L- 的氧羰基化5-己烯醇8/9或14/15。合成分 7 步进行，(+)-1/ (+)-2 的总产率为 6% 和 18%，(-)-1/ (-)- 合成分 6 步进行，总产率为 11% 和 16% 2（来自单丙酮葡萄糖）。由此建立的 goniofufurone (+)-1 及其 7-差向异构体 (+)-2 的绝对构型与所有建议的生物发生前体的绝对构型一致，并允许例如提出 (+)-goniopypyrone 的绝对构型，相关的细胞毒性、双环苯乙烯内酯和潜在生物合成中间体的结构迄今尚未确定。
• A concise synthesis of harzialactone A from d-glucose and revision of absolute stereochemistry
  作者：Hari Babu Mereyala、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(99)00245-1

  日期：1999.6

  Synthesis of 2 by a chiron approach is described starting from monoacetone-D-glucose 4. Absolute stereochemistry of natural harzialactone A 1 (2S,4S) is revised to 2 (2R,4R). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of harzialactone A and its isomers from d-glucose and assignment of absolute stereochemistry
  作者：Hari Babu Mereyala、Maju Joe、Rajendrakumar Reddy Gadikota

  DOI：10.1016/s0957-4166(00)00389-x

  日期：2000.10

  The synthesis of the marine metabolite (3R,5R)-harzialactone A 1 from D-glucose is described. Syntheses of all the isomers (3S,5R)-2, (3R,5S)-3 and (3S,5S)-4 of 1 are also described and the absolute stereochemistry for the natural product 1 is assigned unambiguously. (C) 2000 Elsevier Science Ltd. All rights reserved.