((1S,2R,3R,4S)-4-tert-Butoxycarbonylamino-2,3-dihydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester | 211993-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ((1S,2R,3R,4S)-4-tert-Butoxycarbonylamino-2,3-dihydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S,2R,3R,4S)-4-(tert-butoxycarbonylamino)-2,3-dihydroxy-5-phenoxy-1-(phenoxymethyl)pentyl]carbamate；tert-butyl N-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,6-diphenoxyhexan-2-yl]carbamate
• CAS: 211993-86-1
• 化学式: C₂₈H₄₀N₂O₈
• 分子量: 532.634
• InChiKey: RFDBKMRSPAVGBL-CJRSTVEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((1S,2R,3R,4S)-4-tert-Butoxycarbonylamino-2,3-dihydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 22.83h， 生成 ((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates

  摘要：

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.

  DOI：

  10.1021/jo971562c
• 作为产物：
  描述：

  (4R,5R)-4,5-bis[(1S)-1-azido-2-(4-nitrophenoxy)ethyl]-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 氢气 、 乙酰氯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 ((1S,2R,3R,4S)-4-tert-Butoxycarbonylamino-2,3-dihydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates

  摘要：

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.

  DOI：

  10.1021/jo971562c

文献信息

• New potent C 2 -Symmetric malaria plasmepsin I and II inhibitors
  作者：Karin Oscarsson、Stefan Oscarson、Lotta Vrang、Elizabeth Hamelink、Anders Hallberg、Bertil Samuelsson

  DOI：10.1016/s0968-0896(02)00643-0

  日期：2003.4

  plasmepsin (Plm) I and II inhibitors containing a C(2)-symmetric core structure have been synthesised and tested for protease inhibition activity. These compounds can be prepared using a straightforward synthesis involving a phenol nucleophilic ring opening of a diepoxide. Exemplar compounds synthesised exhibited remarkable inhibitory activity against both Plm I and II, notably 15c with K(i) values of 2

  已经合成了一系列含有C（2）对称核心结构的疟疾纤溶酶（Plm）I和II抑制剂，并测试了其蛋白酶抑制活性。这些化合物可以使用涉及二环氧的酚亲核开环的直接合成来制备。合成的示例化合物对Plm I和II均显示出显着的抑制活性，尤其是15c，其K（i）值分别为2.7nM和0.25nM，并且对组织蛋白酶D的选择性超过100倍。
• HIV-1 Protease Inhibitors Based on Acyclic Carbohydrates
  作者：Guido Zuccarello、Abderrahim Bouzide、Ingemar Kvarnström、Gunilla Niklasson、Stefan C. T. Svensson、Magnus Brisander、Helena Danielsson、Ulrika Nillroth、Anders Karlén、Anders Hallberg、Björn Classon、Bertil Samuelsson

  DOI：10.1021/jo971562c

  日期：1998.7.1

  A series of acyclic Ct-symmetric HIV protease inhibitors readily accessible from D-mannitol have been developed. Several of the compounds synthesized showed significant in vitro activity against HIV-1 protease.