ethyl 4,6-di-O-allyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide | 866322-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-di-O-allyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide
• 英文别名: (2S,3R,4R,5S,6R)-3-azido-2-ethylsulfinyl-4-phenylmethoxy-5-prop-2-enoxy-6-(prop-2-enoxymethyl)oxane
• CAS: 866322-05-6
• 化学式: C₂₁H₂₉N₃O₅S
• 分子量: 435.544
• InChiKey: PIQSDEJBTFNMER-PRSRCKKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  87.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-di-O-allyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide 在 四氮唑 、 盐酸 、 sodium hydroxide 、 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 、 三氟甲磺酸酐 、 氨 、 氢气 、 sodium 、 4-甲基苯磺酸吡啶 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.18h， 生成 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595
• 作为产物：
  描述：

  ethyl 4,6-di-O-allyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到ethyl 4,6-di-O-allyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595

文献信息

• Synthesis of the Core Tetrasaccharide of <i>Trypanosoma </i><i>c</i><i>ruzi</i> Glycoinositolphospholipids: Man<i>p</i>(α1→6)-Man<i>p</i>(α1→4)-6-(2-aminoethylphosphonic acid)-GlcN<i>p</i>(α1→6)-<i>m</i><i>yo</i>-Ins-1-PO₄
  作者：Markus Hederos、Peter Konradsson

  DOI：10.1021/jo0508595

  日期：2005.9.1

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.