ethyl 1,2-O-isopropylidene-3-O-benzyl-5-nitromethyl-5,8-dideoxy-β-L-ido-heptofuranuronate | 1071912-14-5

• 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: ethyl 1,2-O-isopropylidene-3-O-benzyl-5-nitromethyl-5,8-dideoxy-β-L-ido-heptofuranuronate
• 英文别名: ethyl (3R)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-nitrobutanoate
• CAS: 1071912-14-5
• 化学式: C₂₀H₂₇NO₈
• 分子量: 409.436
• InChiKey: FTWDFUVCXXTWTC-IQZDNPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 1,2-O-isopropylidene-3-O-benzyl-5-nitromethyl-5,8-dideoxy-β-L-ido-heptofuranuronate 在 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 3-O-benzyl-5-(benzyloxycarbonyl)-aminomethyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-hepto-1,4-furanose
  参考文献：
  名称：

  Synthesis of new six- and seven-membered 1-N-iminosugars as promising glycosidase inhibitors

  摘要：

  New six- and seven-membered 1-N-iminosugars were prepared from D-glucose by the stereoselective Michael addition of nitromethane to D-glucose derived alpha,beta-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO(4) oxidative cleavage and hydrogenation using 10% Pd(OH)(2)/C, H(2) gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H(2) however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific alpha-galactosidase and moderate alpha-glucosidae inhibitors, respectively, in micro molar range. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.059
• 作为产物：
  描述：

  硝基甲烷 、 (1R,2R,3S,4R)-ethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以87%的产率得到ethyl 1,2-O-isopropylidene-3-O-benzyl-5-nitromethyl-5,8-dideoxy-β-L-ido-heptofuranuronate
  参考文献：
  名称：

  五元和六元氨基环醇的合成：d-葡萄糖衍生的α，β-不饱和酯的立体选择性Michael和Henry反应方法

  摘要：

  将硝基甲烷立体选择性地分子间迈克尔加成到d-葡萄糖衍生的α，β-不饱和酯7中，得到了l-氨基构型的硝酸酯8，这是唯一的酯官能度降低，1,2-丙酮化物裂解和分子内亨利分解的产物。反应，得到只粘膜-nitroinositol 9。虽然减少了8中的酯官能度，1,2-丙酮化物的脱保护，NaIO 4的氧化裂解和分子内的亨利反应提供了硝基环戊醇13。硝基环醇9和13分别转化为羟乙基取代的氨基环己糖醇5和氨基环戊糖醇6。

  DOI：

  10.1016/j.tet.2008.07.049

文献信息

• Synthesis of five and six membered aminocyclitols: stereoselective Michael and Henry reaction approach with d-glucose derived α,β-unsaturated ester
  作者：Chaitali Chakraborty、Vinod P. Vyavahare、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tet.2008.07.049

  日期：2008.9

  The stereoselective intermolecular Michael addition of nitromethane to d-glucose derived α,β-unsaturated ester 7 afforded l-ido-configurated nitroester 8 as the only product that on reduction of the ester functionality, cleavage of 1,2-acetonide and the intramolecular Henry reaction afforded exclusively muco-nitroinositol 9. While reduction of the ester functionality in 8, deprotection of 1,2-acetonide

  将硝基甲烷立体选择性地分子间迈克尔加成到d-葡萄糖衍生的α，β-不饱和酯7中，得到了l-氨基构型的硝酸酯8，这是唯一的酯官能度降低，1,2-丙酮化物裂解和分子内亨利分解的产物。反应，得到只粘膜-nitroinositol 9。虽然减少了8中的酯官能度，1,2-丙酮化物的脱保护，NaIO 4的氧化裂解和分子内的亨利反应提供了硝基环戊醇13。硝基环醇9和13分别转化为羟乙基取代的氨基环己糖醇5和氨基环戊糖醇6。
• Synthesis of new six- and seven-membered 1-N-iminosugars as promising glycosidase inhibitors
  作者：Amit M. Jabgunde、Navnath B. Kalamkar、Sanjay T. Chavan、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.bmc.2011.07.059

  日期：2011.10

  New six- and seven-membered 1-N-iminosugars were prepared from D-glucose by the stereoselective Michael addition of nitromethane to D-glucose derived alpha,beta-unsaturated ester A followed by one pot reduction of nitro/ester functionality and subsequent amine protection to get N-Cbz protected aminol 6. Hydrolysis of 1,2-acetonide and reductive aminocyclization gave seven membered 1-N-iminosugar 5b. While, hydrolysis of 1,2-acetonide followed by NaIO(4) oxidative cleavage and hydrogenation using 10% Pd(OH)(2)/C, H(2) gave six membered 1-N-iminosugar 4a; the hydrogenation using 10% Pd/C-H(2) however, gave N-methyl substituted 1-N-iminosugar 4b. The hydrochloride salts of 4a/4b and 5b were found to be specific alpha-galactosidase and moderate alpha-glucosidae inhibitors, respectively, in micro molar range. (C) 2011 Elsevier Ltd. All rights reserved.