((2R,3R,4S,5S)-3-(benzoyloxy)-4-fluoro-5-((hydroxy(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl benzoate | 916987-63-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ((2R,3R,4S,5S)-3-(benzoyloxy)-4-fluoro-5-((hydroxy(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl benzoate
• CAS: 916987-63-8
• 化学式: C₃₄H₄₂FO₉P
• 分子量: 644.674
• InChiKey: ZVGZPMRDTQNRQZ-GAUACFPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5S)-3-(benzoyloxy)-4-fluoro-5-((hydroxy(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl benzoate 在 甲醇 、 水 、 三乙胺 作用下， 以60%的产率得到trans,trans-farnesyl 2-deoxy-2-fluoro-β-D-arabinofuranosyl phosphate
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates

  摘要：

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.020
• 作为产物：
  描述：

  dibenzyl (3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl) phosphate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 ((2R,3R,4S,5S)-3-(benzoyloxy)-4-fluoro-5-((hydroxy(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)oxy)phosphoryl)oxy)tetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates

  摘要：

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.020