(2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane | 177186-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane
• CAS: 177186-42-4
• 化学式: C₂₃H₃₃NO₃Si
• 分子量: 399.605
• InChiKey: VYKXZVVJNNSGRI-NHCUHLMSSA-N

物化性质

• 沸点：
  452.7±43.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  53.71
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane 在 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 9.5h， 生成 (2S,3R)-3-N-tert-butoxycarbonylamino-4-tert-butyldiphenylsilyloxy-butane-1,2-diol
  参考文献：
  名称：

  Enantiopure aminotriol from d-isoascorbic acid synthesis of

  摘要：

  Enantiopure suitably N,O-protected aminotriol has been prepared from D-isoascorbic acid. The utility of this homochiral building block in the synthesis of (2R,3R)-D-threo-C-18-sphingosine is described via a Wittig reaction on a N,O-protected beta-amino-alpha-hydroxyaldehyde. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00087-0
• 作为产物：
  描述：

  ethyl (R)-2-[(4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl]-2-hydroxyacetate 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 、 tetramethylguanidinum azide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 39.0h， 生成 (2S,3R)-3-amino-4-tert-butyldiphenylsilyloxy-1,2-isopropylidenedioxy-butane
  参考文献：
  名称：

  Enantiopure aminotriol from d-isoascorbic acid synthesis of

  摘要：

  Enantiopure suitably N,O-protected aminotriol has been prepared from D-isoascorbic acid. The utility of this homochiral building block in the synthesis of (2R,3R)-D-threo-C-18-sphingosine is described via a Wittig reaction on a N,O-protected beta-amino-alpha-hydroxyaldehyde. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00087-0

文献信息

• [EN] PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PHOSPHORIBOSYLTRANSFÉRASES ET LEURS UTILISATIONS
  申请人：IND RES LTD

  公开号：WO2012150866A1

  公开（公告）日：2012-11-08

  The invention relates to compounds of formula (I) that are inhibitors of hypoxanthine and/or guanine purine phosphoribosyltransferases and to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and methods of treating diseases or conditions in which it is desirable to inhibit hypoxanthine and/or guanine purine phosphoribosyltransferases. Such diseases include malaria.

  这项发明涉及到式（I）的化合物，这些化合物是次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的抑制剂，以及含有这些化合物的药物组合物、制备这些化合物的方法，以及治疗希望抑制次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的疾病或症状的方法。这些疾病包括疟疾。
• Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase
  作者：Keith Clinch、Douglas R. Crump、Gary B. Evans、Keith Z. Hazleton、Jennifer M. Mason、Vern L. Schramm、Peter C. Tyler

  DOI：10.1016/j.bmc.2013.02.016

  日期：2013.9

  The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantiopure aminotriol from d-isoascorbic acid synthesis of
  作者：Arounarith Tuch、Michèle Sanière、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0957-4166(96)00087-0

  日期：1996.3

  Enantiopure suitably N,O-protected aminotriol has been prepared from D-isoascorbic acid. The utility of this homochiral building block in the synthesis of (2R,3R)-D-threo-C-18-sphingosine is described via a Wittig reaction on a N,O-protected beta-amino-alpha-hydroxyaldehyde. (C) 1996 Elsevier Science Ltd