(5-Cholesten-1α,3β,25-triol)-1,3-diacetat | 50392-31-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (5-Cholesten-1α,3β,25-triol)-1,3-diacetat
• 英文别名: 1α,25-Dihydroxycholesterol-diacetat
• CAS: 50392-31-9
• 化学式: C₃₁H₅₀O₅
• 分子量: 502.735
• InChiKey: VFLWZFJZPVUEMF-GSPSVRGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5-Cholesten-1α,3β,25-triol)-1,3-diacetat 在 二乙胺基三氟化硫 作用下， 以 一氟三氯甲烷 为溶剂， 生成 1α-Acetoxy-25-fluorocholesteryl acetate
  参考文献：
  名称：

  The synthesis and activity in vitro of 25-masked-1α-hydroxylated vitamin D3 analogs

  摘要：

  1alphaHydroxylated-25-masked-vitamin D3 and analogs were synthesized as probes to help evaluate the role of 25-hydroxyl group in hormone-receptor interactions of 1alpha,25-dihydroxyvitamin D3 (13a). Synthetic work on model systems showed that the steroidal 25-hydroxyl group could be easily fluorinated in high yield with diethylaminosulfur trifluoride. Treatment of 25-fluoro compound with acetic acid resulted in both elimination and displacement of fluorine by acetate. The desired 1alpha-hydroxy-25-fluoro-vitamin D3 (14b) was obtained efficiently by fluorination and subsequent deacetylation of 1alpha,25-dihydroxyvitamin D3 1,3-diacetate (13b). Also obtained was a mixture of 1alpha-hydroxyvitamin D3-24- and 25-enes (15b). Both 14b and 15b were 300-400 times less active than 13a in the chick intestinal cytosol protein binding assay, making these analogs similar in potency to 1alpha-hydroxyvitamin D3 in vitro. The essentially equivalent activity of 14b and 15b with 1alpha-hydroxyvitamin D3 indicates that in the absence of a 25-hydroxyl group some alterations to the side chain carbons of 13a may be tolerated without further weakening analog-protein interactions. The fluoroanalog 14b was also about 250 times less potent than 13a in stimulating bone resorption in vitro. These compounds should prove to be valuable tools in aiding understanding of the salient structural features of the vitamin D3 metabolites.

  DOI：

  10.1016/0039-128x(78)90058-2
• 作为产物：
  描述：

  25-羟基胆甾醇 在 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 水 、 双氧水 、 lithium 、 氯化铵 、 对甲苯磺酸 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 苯 为溶剂， 反应 60.25h， 生成 (5-Cholesten-1α,3β,25-triol)-1,3-diacetat
  参考文献：
  名称：

  EINE ergiebige Herstellung冯1α，3β二羟基Δ 5 -steroiden第三人以Reduktion冯1α，2α环氧-4,6-二烯-3- onen MIT锂在Ammoniak †

  摘要：

  用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨

  DOI：

  10.1002/hlca.19810640621

文献信息

• Synthesis of Active Forms of Vitamin D. III. Synthesis of 1α, 25-Dihydroxycholesterol
  作者：JULIETA RUBIO-LIGHTBOURN、MASUO MORISAKI、NOBUO IKEKAWA

  DOI：10.1248/cpb.21.1854

  日期：——