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1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3 | 874635-39-9

中文名称
——
中文别名
——
英文名称
1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3
英文别名
1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3
1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3化学式
CAS
874635-39-9
化学式
C37H62N2O5
mdl
——
分子量
614.91
InChiKey
ZFVHUOACHONEKH-PEWGNKSHSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    8.77
  • 重原子数:
    44.0
  • 可旋转键数:
    9.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.78
  • 拓扑面积:
    96.89
  • 氢给体数:
    3.0
  • 氢受体数:
    5.0

反应信息

  • 作为反应物:
    描述:
    1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3丙酮 为溶剂, 反应 4.0h, 以43%的产率得到{(1R,3S)-3-tert-Butoxycarbonylamino-5-[2-[(1R,3aS,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl}-carbamic acid tert-butyl ester
    参考文献:
    名称:
    Versatile synthesis and biological evaluation of 1,3-diamino-substituted 1α,25-dihydroxyvitamin D3 analogues
    摘要:
    A concise route to 1 alpha,3 beta-diamino-25-hydroxy-3-deoxyvitamin D-3 (5) and 1 beta,3 alpha-diamino-25-hydroxy-3-deoxyvitamin D, (6) has been developed starting from (R)- or (S)-carvone for the construction of the modified A-ring fragments. The conversion of the hydroxyl group to amine function with complete inversion of the configuration was efficiently accomplished by Mitsunobu reaction using phthalimide as nucleophile or activation of the hydroxyl group as mesylate followed by reaction with NaN3. Diamino 5 and 6 as well as monoamino 3, 4 X and 31 vitamin D3 derivatives have shown poor binding to VDR compared with 1 alpha,25-dihydroxyvitamin D3. The most active compound in the inhibition of MCF-7 cell proliferation and HL 60 cell differentiation was 1 alpha-amino analogue 3. Also, very low in vivo calcemic effects of derivatives 3 and 4 were found. (c) 2005 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2005.09.009
  • 作为产物:
    描述:
    (3S,5R)-1-ethynyl-2-methyl-3,5-bis(phthalimido)cyclohex-1-ene喹啉 、 Lindlar's catalyst 、 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 四丁基氟化铵氢气碳酸氢钠二乙胺甲胺 作用下, 以 四氢呋喃甲醇乙醇正己烷氯仿N,N-二甲基甲酰胺 为溶剂, 反应 73.33h, 生成 1α,3β-bis[(tert-butoxycarbonyl)amino]-25-hydroxy-3-deoxyprevitamin D3
    参考文献:
    名称:
    Versatile synthesis and biological evaluation of 1,3-diamino-substituted 1α,25-dihydroxyvitamin D3 analogues
    摘要:
    A concise route to 1 alpha,3 beta-diamino-25-hydroxy-3-deoxyvitamin D-3 (5) and 1 beta,3 alpha-diamino-25-hydroxy-3-deoxyvitamin D, (6) has been developed starting from (R)- or (S)-carvone for the construction of the modified A-ring fragments. The conversion of the hydroxyl group to amine function with complete inversion of the configuration was efficiently accomplished by Mitsunobu reaction using phthalimide as nucleophile or activation of the hydroxyl group as mesylate followed by reaction with NaN3. Diamino 5 and 6 as well as monoamino 3, 4 X and 31 vitamin D3 derivatives have shown poor binding to VDR compared with 1 alpha,25-dihydroxyvitamin D3. The most active compound in the inhibition of MCF-7 cell proliferation and HL 60 cell differentiation was 1 alpha-amino analogue 3. Also, very low in vivo calcemic effects of derivatives 3 and 4 were found. (c) 2005 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2005.09.009
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同类化合物

(5β)-17,20:20,21-双[亚甲基双(氧基)]孕烷-3-酮 (5α)-2′H-雄甾-2-烯并[3,2-c]吡唑-17-酮 (3β,20S)-4,4,20-三甲基-21-[[[三(异丙基)甲硅烷基]氧基]-孕烷-5-烯-3-醇-d6 (25S)-δ7-大发酸 (20R)-孕烯-4-烯-3,17,20-三醇 (11β,17β)-11-[4-({5-[(4,4,5,5,5-五氟戊基)磺酰基]戊基}氧基)苯基]雌二醇-1,3,5(10)-三烯-3,17-二醇 齐墩果酸衍生物1 黄麻属甙 黄芪皂苷III 黄芪皂苷 II 黄芪甲苷 IV 黄芪甲苷 黄肉楠碱 黄果茄甾醇 黄杨醇碱E 黄姜A 黄夹苷B 黄夹苷 黄夹次甙乙 黄夹次甙乙 黄夹次甙丙 黄体酮环20-(乙烯缩醛) 黄体酮杂质EPL 黄体酮杂质1 黄体酮杂质 黄体酮杂质 黄体酮EP杂质M 黄体酮EP杂质G(RRT≈2.53) 黄体酮EP杂质F 黄体酮6-半琥珀酸酯 黄体酮 17alpha-氢过氧化物 黄体酮 11-半琥珀酸酯 黄体酮 麦角甾醇葡萄糖苷 麦角甾醇氢琥珀酸盐 麦角甾烷-6-酮,2,3-环氧-22,23-二羟基-,(2b,3b,5a,22R,23R,24S)-(9CI) 麦角甾烷-3,6,8,15,16-五唑,28-[[2-O-(2,4-二-O-甲基-b-D-吡喃木糖基)-a-L-呋喃阿拉伯糖基]氧代]-,(3b,5a,6a,15b,16b,24x)-(9CI) 麦角甾烷-26-酸,5,6:24,25-二环氧-14,17,22-三羟基-1-羰基-,d-内酯,(5b,6b,14b,17a,22R,24S,25S)-(9CI) 麦角甾-8-烯-3-醇 麦角甾-8,24(28)-二烯-26-酸,7-羟基-4-甲基-3,11-二羰基-,(4a,5a,7b,25S)- 麦角甾-7,22-二烯-3-酮 麦角甾-7,22-二烯-17-醇-3-酮 麦角甾-5,24-二烯-26-酸,3-(b-D-吡喃葡萄糖氧基)-1,22,27-三羟基-,d-内酯,(1a,3b,22R)- 麦角甾-5,22,25-三烯-3-醇 麦角甾-4,6,8(14),22-四烯-3-酮 麦角甾-1,4-二烯-3-酮,7,24-二(乙酰氧基)-17,22-环氧-16,25-二羟基-,(7a,16b,22R)-(9CI) 麦角固醇 麦冬皂苷D 麦冬皂苷D 麦冬皂苷 B