[(2R)-2,3-dihydroxypropyl] 9H-fluoren-9-ylmethyl carbonate | 194796-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(2R)-2,3-dihydroxypropyl] 9H-fluoren-9-ylmethyl carbonate
• CAS: 194796-98-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: MYXQOYYGFHRLJN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  棕榈酸 、 [(2R)-2,3-dihydroxypropyl] 9H-fluoren-9-ylmethyl carbonate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到(R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)propane-1,2-diyl dipalmitate
  参考文献：
  名称：

  A new protecting group: 9-fluorenylmethoxycarbonyl (FMOC) in the synthesis of 1,2-diacylglycerols

  摘要：

  The synthesis of 1,2-L-dipalmitoyl-sn-glycerol, 1,2-L-distearoyl-sn-glycerol and 1,2-L-dioleoyl-sn-glycerol are described here using 9-fluorenylmethoxycarbonyl (FMOC) group for protection of the S-position of glycerol which can be selectively removed by Et3N treatment on the overall 60-70% yield based on 1,2-isopropylidene-sn-glycerol. Little or no acyl migration occured during deprotection and purification. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00034-0
• 作为产物：
  描述：

  Carbonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 9H-fluoren-9-ylmethyl ester 在 甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以89%的产率得到[(2R)-2,3-dihydroxypropyl] 9H-fluoren-9-ylmethyl carbonate
  参考文献：
  名称：

  A new protecting group: 9-fluorenylmethoxycarbonyl (FMOC) in the synthesis of 1,2-diacylglycerols

  摘要：

  The synthesis of 1,2-L-dipalmitoyl-sn-glycerol, 1,2-L-distearoyl-sn-glycerol and 1,2-L-dioleoyl-sn-glycerol are described here using 9-fluorenylmethoxycarbonyl (FMOC) group for protection of the S-position of glycerol which can be selectively removed by Et3N treatment on the overall 60-70% yield based on 1,2-isopropylidene-sn-glycerol. Little or no acyl migration occured during deprotection and purification. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00034-0

文献信息

• An Improved Synthesis of 1-β-D-Arabinofuranosylcytosine 5′-Phosphate-L-1,2-diacylglycerols
  作者：Ágnes Nyilas

  DOI：10.1080/07328319808004734

  日期：1998.9

  5'-O-MMTr-cytosine arabinoside was prepared on a large scale from 5'-0-MMTr-cytidine with diphenyl carbonate via 5'-protected cytidine - 2',3'-carbonate -- aracytidine-2',2-anhydro derivative at a 67 % yield. The synthesis of 1,2-L-dipalmitoyl-sn-glycerol, 1,2-L-distearoyl-sn-glycerol and 1,2-L-dioleoyl-sn-glycerol described here using 9-fluorenylmethoxycarbonyl (FMOC) group for protection of 3-position of glycerol which can be selectively removed by Et3N treatment on the overall 60-70 % yield based on 1,2,-isopropilidene-sn-glycerol. These glycerols were phosphorylated first with 2-chlorophenyl-phosphoro-bis-triazolide quantitatively(1) in order to avoid acyl migration, then the glycerophosphate intermediates were condensed with 2',3',N-4-trileulinyl-1-beta-D-arabinofuranosylcytosine in the presence of 2-mesytilenesulphonyl chloride (MsCl) and 1-methylimidazole (MeIm)- which was used in the coupling of nucleotides(2)- in an 85-95 % yield compared with the low yielding diester method of Ryu(3.) Deblocking was carried out in two steps with tetrabutylammonium fluoride (TBAF) and hydrazine hydrate, producing target compouns (14a, 14b, 14c) at a 50 % yield.