ethyl 2,6-anhydro-3-deoxy-7,8-O-isopropylidene-D-gluco-D-glycero-octanoate | 259683-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,6-anhydro-3-deoxy-7,8-O-isopropylidene-D-gluco-D-glycero-octanoate
• 英文别名: ethyl (2R,4R,5S,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,5-dihydroxyoxane-2-carboxylate
• CAS: 259683-46-0
• 化学式: C₁₃H₂₂O₇
• 分子量: 290.313
• InChiKey: JISSCVKCLNYBTE-MVCUBJFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,6-anhydro-3-deoxy-7,8-O-isopropylidene-D-gluco-D-glycero-octanoate 在 吡啶 、 sodium tetrahydroborate 、 高碘酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 ethyl 2,6-anhydro-3-deoxy-4,5-O-diacetyl-D-gluco-heptanoate
  参考文献：
  名称：

  An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-GlucoAnd D-Allo-Heptanoates

  摘要：

  An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain, in situ reduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.

  DOI：

  10.1080/07328309908544055
• 作为产物：
  描述：

  ethyl (2R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,6-dihydro-2H-pyran-2-carboxylate 在 potassium dioxotetrahydroxoosmate(VI) 、 (DHQD-PHAL) sodium tetrahydroborate 、 碳酸氢钠 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 10.5h， 生成 ethyl 2,6-anhydro-3-deoxy-7,8-O-isopropylidene-D-gluco-D-glycero-octanoate
  参考文献：
  名称：

  An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-GlucoAnd D-Allo-Heptanoates

  摘要：

  An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain, in situ reduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.

  DOI：

  10.1080/07328309908544055

文献信息

• An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-<i>Gluco</i>And D-<i>Allo</i>-Heptanoates
  作者：Lian-Sheng Li、Yikang Wu、Yu-Lin Wu

  DOI：10.1080/07328309908544055

  日期：1999.1

  An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain, in situ reduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.