prop-2-enyl 2-[(2S,3S,4S,5R,6R)-6-[bis(phenylmethoxy)phosphoryloxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyacetate | 1428872-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: prop-2-enyl 2-[(2S,3S,4S,5R,6R)-6-[bis(phenylmethoxy)phosphoryloxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyacetate
• CAS: 1428872-88-1
• 化学式: C₄₆H₄₉O₁₁P
• 分子量: 808.862
• InChiKey: URIYOYAHHQGWLU-USCUKMNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  58
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2-[(2S,3S,4S,5R,6R)-6-[bis(phenylmethoxy)phosphoryloxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyacetate 在 吗啉 、 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-[(2S,3S,4S,5R,6R)-6-[bis(phenylmethoxy)phosphoryloxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyacetic acid
  参考文献：
  名称：

  Synthesis of novel bivalent mimetic ligands for mannose-6-phosphate receptors

  摘要：

  Mannose-6-phosphate (M6P)-containing N-linked glycans are essential signaling molecules for sorting hydrolases in eukaryotic cells. Their receptors, especially the cation-independent M6P receptors (CI-MPRs), have emerged as promising protein targets for targeted drug delivery for the treatment of lysosomal storage disease and liver fibrosis. In this Letter, we describe the design and synthesis of novel bivalent mimetic ligands for CI-MPRs. We report that for the first time, a newly-discovered binding motif, GlcNAc-M6P, has been incorporated in mimetic ligands. M6P- and GlcNAc-M6P-containing building blocks, equipped with NH2 and CO2H handles, have been prepared and assembled with an ornithine linker through amide coupling reactions. Efficient global deprotection protocols have also been developed which have been showcased in the synthesis of our novel bivalent mimetic ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.068
• 作为产物：
  描述：

  allyl-2,3,4-tri-O-benzyl-6-O-trityl-α-D-mannopyranoside 在 四氮唑 、 叔丁基过氧化氢 、 ruthenium trichloride 、 sodium periodate 、 iron(III) chloride hexahydrate 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.0h， 生成 prop-2-enyl 2-[(2S,3S,4S,5R,6R)-6-[bis(phenylmethoxy)phosphoryloxymethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyacetate
  参考文献：
  名称：

  Synthesis of novel bivalent mimetic ligands for mannose-6-phosphate receptors

  摘要：

  Mannose-6-phosphate (M6P)-containing N-linked glycans are essential signaling molecules for sorting hydrolases in eukaryotic cells. Their receptors, especially the cation-independent M6P receptors (CI-MPRs), have emerged as promising protein targets for targeted drug delivery for the treatment of lysosomal storage disease and liver fibrosis. In this Letter, we describe the design and synthesis of novel bivalent mimetic ligands for CI-MPRs. We report that for the first time, a newly-discovered binding motif, GlcNAc-M6P, has been incorporated in mimetic ligands. M6P- and GlcNAc-M6P-containing building blocks, equipped with NH2 and CO2H handles, have been prepared and assembled with an ornithine linker through amide coupling reactions. Efficient global deprotection protocols have also been developed which have been showcased in the synthesis of our novel bivalent mimetic ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.068

文献信息

• Synthesis of novel bivalent mimetic ligands for mannose-6-phosphate receptors
  作者：Yunpeng Liu、Jared Marshall、Qiong Li、Nicola Edwards、Gong Chen

  DOI：10.1016/j.bmcl.2013.02.068

  日期：2013.4

  Mannose-6-phosphate (M6P)-containing N-linked glycans are essential signaling molecules for sorting hydrolases in eukaryotic cells. Their receptors, especially the cation-independent M6P receptors (CI-MPRs), have emerged as promising protein targets for targeted drug delivery for the treatment of lysosomal storage disease and liver fibrosis. In this Letter, we describe the design and synthesis of novel bivalent mimetic ligands for CI-MPRs. We report that for the first time, a newly-discovered binding motif, GlcNAc-M6P, has been incorporated in mimetic ligands. M6P- and GlcNAc-M6P-containing building blocks, equipped with NH2 and CO2H handles, have been prepared and assembled with an ornithine linker through amide coupling reactions. Efficient global deprotection protocols have also been developed which have been showcased in the synthesis of our novel bivalent mimetic ligands. (C) 2013 Elsevier Ltd. All rights reserved.