Phenyl-carbamic acid (2R,3R,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester | 115533-37-4

• 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: Phenyl-carbamic acid (2R,3R,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester
• CAS: 115533-37-4
• 化学式: C₂₃H₃₅NO₇
• 分子量: 437.533
• InChiKey: VKOCGLFOLUHXSE-REYORBRHSA-N

物化性质

• 沸点：
  583.3±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  117.48
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Phenyl-carbamic acid (2R,3R,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester 在 吡啶 、 tetrafluoroboric acid 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 (3aS,4R,5aR,8R,9aR,9bS)-4-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-2-one
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.

  DOI：

  10.1016/s0008-6215(00)90561-5
• 作为产物：
  描述：

  D-薄荷醇 在 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Phenyl-carbamic acid (2R,3R,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119

  摘要：

  DOI：