((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester | 214556-67-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,3S,4R)-1,3,4-trihydroxy-4-phenylbutan-2-yl]carbamate
• CAS: 214556-67-9
• 化学式: C₁₅H₂₃NO₅
• 分子量: 297.351
• InChiKey: LFSZSAVDIXXWBG-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 Dodecanoic acid ((1S,2S,3R)-2,3-dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-amide
  参考文献：
  名称：

  Stereoselective Synthesis and Structure−Activity Relationship of Novel Ceramide Trafficking Inhibitors. (1R,3R)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and Its Analogues

  摘要：

  New ceramide trafficking inhibitors, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) and a series of its analogues, were synthesized in diastereomerically and enantiomerically pure forms, and the structure-activity relationship was investigated. These analogues were stereoselectively synthesized via catalytic enantioselective Mannich-type reactions using a Cu(II)-chiral diamine 4 complex. Analysis of HPA-12 analogues having various lengths of the amide side chain showed that the optimal chain length for the inhibition of sphingomyelin biosynthesis is 13 with an IC50 of similar to50 nM. Masking of the hydroxy group at the 2'- or 3-position of HPA-12 was carried out by methylation, and it was revealed that these hydroxy groups were essential for the activity. Installation of another hydroxy group onto HPA-12 at the same position as that in the natural ceramide was also conducted, but no enhancement of the activity was observed.

  DOI：

  10.1021/jm0300779
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 AD-mix-α 、 Amberlite IR-120 、 甲基磺酰胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 51.5h， 生成 ((1S,2S,3R)-2,3-Dihydroxy-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  使用不对称二羟基化技术快速有效地合成植物鞘氨醇

  摘要：

  描述了通过使用衍生自1-丝氨酸的旋光性烯烃的不对称二羟基化来简短合成植物鞘氨醇衍生物及其立体异构体。

  DOI：

  10.1016/s0040-4020(98)00615-2