1-pivalic acid (2S,3S)-3-hydroxy-2-[(R)-1-(methoxymethoxy)allyl]hex-5-ynyl ester | 288380-95-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-pivalic acid (2S,3S)-3-hydroxy-2-[(R)-1-(methoxymethoxy)allyl]hex-5-ynyl ester
• 英文别名: [(2S,3R)-3-hydroxy-2-[(1R)-1-(methoxymethoxy)prop-2-enyl]hex-5-ynyl] 2,2-dimethylpropanoate
• CAS: 288380-95-0
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: YSDXUZSDEJYULL-BFHYXJOUSA-N

物化性质

• 沸点：
  381.7±42.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-pivalic acid (2S,3S)-3-hydroxy-2-[(R)-1-(methoxymethoxy)allyl]hex-5-ynyl ester 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 叔丁醇 为溶剂， 反应 76.67h， 生成 (3R,4S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-butylnon-1-en-7-yne
  参考文献：
  名称：

  Efficient and Versatile Synthesis of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D₃ Analogues and Their Docking to Vitamin D Receptors

  摘要：

  Novel 2 alpha -substituted 1 alpha ,25-dihydroxyvitamin D-3 analogues with 2 alpha -alkyl and 2 alpha -hydroxyalkyl groups were systematically synthesized from D-xylose. Their conformation on binding to the ligand binding domain (LBD) of the vitamin D receptor was analyzed. It has been found that the 2 alpha -hydroxypropyl group best fits the cavity of the LBD, and the binding activity is three times higher than that for the natural hormone.

  DOI：

  10.1021/jo010375i
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 20percent Pd(OH)2/C 咪唑 、 盐酸 、 sodium hydroxide 、 正丁基锂 、 4 A molecular sieve 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 9-硼双环[3.3.1]壬烷 、 三苯基膦 、 pyridinium chlorochromate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 76.26h， 生成 1-pivalic acid (2S,3S)-3-hydroxy-2-[(R)-1-(methoxymethoxy)allyl]hex-5-ynyl ester
  参考文献：
  名称：

  Efficient and Versatile Synthesis of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D₃ Analogues and Their Docking to Vitamin D Receptors

  摘要：

  Novel 2 alpha -substituted 1 alpha ,25-dihydroxyvitamin D-3 analogues with 2 alpha -alkyl and 2 alpha -hydroxyalkyl groups were systematically synthesized from D-xylose. Their conformation on binding to the ligand binding domain (LBD) of the vitamin D receptor was analyzed. It has been found that the 2 alpha -hydroxypropyl group best fits the cavity of the LBD, and the binding activity is three times higher than that for the natural hormone.

  DOI：

  10.1021/jo010375i

文献信息

• Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues
  作者：Yoshitomo Suhara、Ken-ichi Nihei、Hirokazu Tanigawa、Toshie Fujishima、Katsuhiro Konno、Kimie Nakagawa、Toshio Okano、Hiroaki Takayama

  DOI：10.1016/s0960-894x(00)00189-x

  日期：2000.5

  Novel 2 alpha-substituted 1 alpha,25-dihydroxyvitamin D-3 analogues were efficiently synthesized and their biological activities were evaluated. 2 alpha-Methyl-1 alpha,25-dihydroxyvitamin D-3 (2), whose unique biological activities were previously reported, was modified to 2 alpha-alkyl (ethyl and propyl) and 2 alpha-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2 alpha-Hydroxypropyl-1 alpha,25-dihydroxyvitamin D-3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.