methyl 6-O-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2,3-di-O-benzyl-α-D-glucopyranoside | 866322-06-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2,3-di-O-benzyl-α-D-glucopyranoside
• 英文别名: benzyl N-[2-[[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxy-phenylmethoxyphosphoryl]ethyl]carbamate
• CAS: 866322-06-7
• 化学式: C₃₈H₄₄NO₁₀P
• 分子量: 705.742
• InChiKey: MKKOQMGNIQZVPZ-SDALRBMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 6-O-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2,3-di-O-benzyl-α-D-glucopyranoside 在 氨 、 sodium 、 DMTST 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 methyl (α-D-mannopyranosyl)-(1->4)-6-O-((2-aminoethyl)phosphonic acid)-α-D-glucopyranoside
  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：

  (2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl 6-O-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2,3-di-O-benzyl-α-D-glucopyranoside
  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.