dibenzyl (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate | 1422670-93-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dibenzyl (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate
• 英文别名: dibenzyl [(2S,3S,4R,5R)-3,4-bis[[tert-butyl(diphenyl)silyl]oxy]-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl] phosphate
• CAS: 1422670-93-6
• 化学式: C₆₇H₇₇O₈PSi₃
• 分子量: 1125.57
• InChiKey: MTZVKHVCABVHNT-SBDLQUGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.74
• 重原子数：
  79
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dibenzyl (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate 、 三乙胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以98%的产率得到bis(triethylammonium) (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate
  参考文献：
  名称：

  Synthesis of Lipid-Linked Arabinofuranose Donors for Glycosyltransferases

  摘要：

  Mycobacteria and corynebacteria use decaprenylphosphoryl-beta-D-arabinofuranose (DPA) as a critical cell wall building block. Arabinofuranosyltransferases that process this substrate to mediate cell wall assembly have served as drug targets, but little is known about the substrate specificity of any of these enzymes. To probe substrate recognition of DPA, we developed a general and efficient synthetic route to beta-D-arabinofuranosyl phosphodiesters. In this approach, the key glycosyl phosphodiester bond-forming reaction proceeds with high beta-selectivity In addition to its stereoselectivity, our route provides the means to readily access a variety of different lipid analogues, including aliphatic and polyprenyl substrates.

  DOI：

  10.1021/jo302507p
• 作为产物：
  描述：

  2,3,5-tri-O-(tert-butyldiphenylsilyl)-D-arabinofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 三甲基溴硅烷 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.5h， 生成 dibenzyl (2,3,5-tri-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl) phosphate 、 dibenzyl (2,3,5-tri-O-tert-butyldiphenylsilyl-β-D-arabinofuranosyl) phosphate
  参考文献：
  名称：

  Synthesis of Lipid-Linked Arabinofuranose Donors for Glycosyltransferases

  摘要：

  Mycobacteria and corynebacteria use decaprenylphosphoryl-beta-D-arabinofuranose (DPA) as a critical cell wall building block. Arabinofuranosyltransferases that process this substrate to mediate cell wall assembly have served as drug targets, but little is known about the substrate specificity of any of these enzymes. To probe substrate recognition of DPA, we developed a general and efficient synthetic route to beta-D-arabinofuranosyl phosphodiesters. In this approach, the key glycosyl phosphodiester bond-forming reaction proceeds with high beta-selectivity In addition to its stereoselectivity, our route provides the means to readily access a variety of different lipid analogues, including aliphatic and polyprenyl substrates.

  DOI：

  10.1021/jo302507p

文献信息

• Synthesis of Lipid-Linked Arabinofuranose Donors for Glycosyltransferases
  作者：Matthew B. Kraft、Mario A. Martinez Farias、Laura L. Kiessling

  DOI：10.1021/jo302507p

  日期：2013.3.1

  Mycobacteria and corynebacteria use decaprenylphosphoryl-beta-D-arabinofuranose (DPA) as a critical cell wall building block. Arabinofuranosyltransferases that process this substrate to mediate cell wall assembly have served as drug targets, but little is known about the substrate specificity of any of these enzymes. To probe substrate recognition of DPA, we developed a general and efficient synthetic route to beta-D-arabinofuranosyl phosphodiesters. In this approach, the key glycosyl phosphodiester bond-forming reaction proceeds with high beta-selectivity In addition to its stereoselectivity, our route provides the means to readily access a variety of different lipid analogues, including aliphatic and polyprenyl substrates.