phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside | 698371-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-nitro-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane
• CAS: 698371-42-5
• 化学式: C₃₃H₃₃NO₆S
• 分子量: 571.694
• InChiKey: HRQQLRWNQFLMOD-UPYFENACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside 在 4-硝基苯亚磺酰氯 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 isopropyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  2-Nitro-thioglycosides: α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors

  摘要：

  Michael-type addition of thiolates to 2-nitro-D-glucal or to 2-nitro-D-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the alpha- or preferentially the beta-anomers, respectively. Addition of achiral and chiral thiourea derivatives to the reaction mixture increased the reaction rate; the outcome is substrate-controlled. The 2-deoxy-2-nitro-1-thioglycosides are excellent glycosyl donors under arylsulfenyl chloride/silver triflate (ArSCl/AgOTf) activation, and they provide, anchimerically assisted by the nitro group, mostly beta-glycosides.

  DOI：

  10.1021/acs.orglett.5b00295
• 作为产物：
  描述：

  苯硫酚 、 3,4,6-tri-O-benzyl-2-nitro-D-glucal 在 4-吡咯烷基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  通过2-硝基糖的立体选择性迈克尔型加成制得2-氨基-β-d-半乳糖-和-吡喃葡萄糖苷的有效途径

  摘要：

  在CH 2 Cl 2中DMAP或PPY的催化下，亲核试剂向2-硝基半乳糖或2-硝基葡萄糖的迈克尔型加成反应导致相应的β-半乳糖或吡喃葡萄糖苷具有良好的收率和立体选择性，而β-半乳糖或-吡喃葡萄糖苷已是这些化合物的现成物质。具有生物学意义的β- d-半乳糖胺和-葡萄糖胺单元。

  DOI：

  10.1021/jo900609s

文献信息

• 2-Nitro Thioglycoside Donors:  Versatile Precursors of β-<scp>d</scp>-Glycosides of Aminosugars
  作者：Nadine Barroca、Richard R. Schmidt

  DOI：10.1021/ol049729t

  日期：2004.5.1

  2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.
• 2-Nitro-thioglycosides: α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors
  作者：Peng Peng、Yiqun Geng、Inigo Göttker-Schnetmann、Richard R. Schmidt

  DOI：10.1021/acs.orglett.5b00295

  日期：2015.3.20

  Michael-type addition of thiolates to 2-nitro-D-glucal or to 2-nitro-D-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the alpha- or preferentially the beta-anomers, respectively. Addition of achiral and chiral thiourea derivatives to the reaction mixture increased the reaction rate; the outcome is substrate-controlled. The 2-deoxy-2-nitro-1-thioglycosides are excellent glycosyl donors under arylsulfenyl chloride/silver triflate (ArSCl/AgOTf) activation, and they provide, anchimerically assisted by the nitro group, mostly beta-glycosides.
• An Efficient Route toward 2-Amino-β-<scp>d</scp>-galacto- and -glucopyranosides via Stereoselective Michael-Type Addition of 2-Nitroglycals
  作者：Weihua Xue、Jiansong Sun、Biao Yu

  DOI：10.1021/jo900609s

  日期：2009.7.17

  Under the catalysis of DMAP or PPY in CH2Cl2, the Michael-type addition of nucleophiles to 2-nitrogalactal or 2-nitroglucal leads in excellent yields and stereoselectivity to the corresponding β-galacto- or -glucopyranosides, which are ready precursors to the biologically significant β-d-galactosamine and -glucosamine units.

  在CH 2 Cl 2中DMAP或PPY的催化下，亲核试剂向2-硝基半乳糖或2-硝基葡萄糖的迈克尔型加成反应导致相应的β-半乳糖或吡喃葡萄糖苷具有良好的收率和立体选择性，而β-半乳糖或-吡喃葡萄糖苷已是这些化合物的现成物质。具有生物学意义的β- d-半乳糖胺和-葡萄糖胺单元。