3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol | 136465-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol
• 英文别名: [(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl] 4-methylbenzenesulfonate
• CAS: 136465-96-8
• 化学式: C₁₇H₁₉N₃O₄S
• 分子量: 361.422
• InChiKey: DXASRSZFCYHEBB-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol 在 palladium on activated charcoal 、 氢气 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 102.0h， 生成 (2R,3S)-3-Cbz-amino-2-hydroxy-4-phenyl-1-benzylaminobutane
  参考文献：
  名称：

  Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

  摘要：

  Lysosomes are involved in protein turnover and removing misfolded species, and their enzymes have the potential to offset the defect in proteolytic clearance that contributes to the age-related dementia Alzheimer's disease (AD). The weak cathepsin B and L inhibitor Z-Phe-Ala-diazomethylketone (PADK) enhances lysosomal cathepsin levels at low concentrations, thereby eliciting protective clearance of PHF-tau and A beta 42 in the hippocampus and other brain regions. Here, a class of positive modulators is established with compounds decoupled from the cathepsin inhibitory properties. We utilized PADK as a departure point to develop nonpeptidic structures with the hydroxyethyl isostere. The first-in-class modulators SD1002 and SD1003 exhibit: : improved levels of cathepsin up-regulation but almost complete removal of cathepsin inhibitory properties as compared to PADK. Isomers of the lead compound SD1002 were synthesized, and the modulatory activity was determined to be stereoselective. In addition, the lead compound was tested in transgenic mice with results indicating protection against AD-type protein accumulation pathology.

  DOI：

  10.1021/ml300197h
• 作为产物：
  描述：

  [(2R,3R)-3-(苯基甲基)环氧乙烷-2-基]甲醇 在 吡啶 、 4-二甲氨基吡啶 、 Ti(N3)2(OiPr)2 作用下， 以 苯 为溶剂， 生成 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol
  参考文献：
  名称：

  A concise, general enantioselective synthetic route to 2(R)- and 2(S)-[1′(S)-azido-2-phenylethyl]oxirane and related epoxides

  摘要：

  利用 Sharpless 不对称环氧化，然后以 [Ti(OPri)2(N3)2] 为关键步骤进行区域选择性叠氮化物置换，以 > 95% 对映体过量 (e.e.) 构建标题环氧乙烷。

  DOI：

  10.1039/c39930000737

文献信息

• Alcohols
  申请人：Hoffmann-La Roche Inc.

  公开号：US05451678A1

  公开（公告）日：1995-09-19

  Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)-, --N(acyl)- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.

  新型醇类的化学式为##STR1##其中R.sup.a是偶氮基或邻苯二甲酰亚胺基，R.sup.4是烷基、环烷基、环烷基烷基、芳香族或芳基烷基，R.sup.7和R.sup.8一起是三亚甲基或四亚甲基基团，该基团可选择地被羟基、烷氧羰胺基或酰胺基取代，或其中一个-CH.sub.2-基团被-NH-、-N(烷氧羰基)-、-N(酰基)-或-S-取代，或携带融合的环烷烃、芳香族或杂芳环，并且R.sup.9是烷氧羰基、单烷基氨基甲酰基、单芳基氨基甲酰基、单芳基氨基甲酰基或化学式##STR2##中的基团，其中R.sup.10和R.sup.11各自是烷基，还描述了它们的制造方法。这些醇类可用作中间体，例如在制造具有抗病毒活性的氨基酸衍生物时。
• Oxirane intermediates for novel alcohols
  申请人：Hoffmann-La Roche Inc.

  公开号：US05508430A1

  公开（公告）日：1996-04-16

  Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.

  本发明涉及一种新型醇，其化学式为##STR1##其中R.sup.a为偶氮基或邻苯二甲酰亚胺基，R.sup.4为烷基、环烷基、环烷基烷基、芳基或芳基烷基，R.sup.7和R.sup.8共同为三亚甲基或四亚甲基基团，该基团可以被羟基、烷氧羰基氨基或酰胺基取代，或其中一个--CH.sub.2--基团被--NH--、--N(烷氧羰基)--、--N(酰基)--或--S--取代，或者带有融合的环烷基、芳香基或杂芳基环，R.sup.9为烷氧羰基、单烷基氨基甲酰基、单芳基氨基甲酰基、单芳基甲酰基或式中R.sup.10和R.sup.11各自为烷基的基团。同时，本发明还涉及一种制备这些醇的方法。这些醇可用作中间体，例如在制备具有抗病毒活性的氨基酸衍生物时。
• A simple and inexpensive procedure for low valent copper mediated benzylation of aldehydes in wet medium: synthesis of protease inhibitor synthon
  作者：Angshuman Chattopadhyay、Akhil Dubey、Dibakar Goswami

  DOI：10.3998/ark.5550190.0011.912

  日期：——

  An operationally simple, inexpensive and efficient procedure for benzylation of aldehydes in wet medium has been developed that was mediated with low valent copper, prepared in situ through spontaneous reduction of CuCl2-2H(2)O with magnesium in situ. Notably, copper mediated benzylation of 3h took place with good syn selectivity that was opposite to that for the corresponding Grignard addition. Finally, homobenzyl alcohol 5a was elegantly transformed into a known protease inhibitor synthon I.
• Synthesis of Conformationally Restricted Mimetics of γ-Turns and Incorporation into Desmopressin, an Analogue of the Peptide Hormone Vasopressin
  作者：Kay Brickmann、ZhongQing Yuan、Ingmar Sethson、Peter Somfai、Jan Kihlberg

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2241::aid-chem2241>3.0.co;2-l

  日期：1999.8.2
• Expedient Method for the Solid-Phase Synthesis of Aspartic Acid Protease Inhibitors Directed toward the Generation of Libraries
  作者：Ellen K. Kick、Jonathan A. Ellman

  DOI：10.1021/jm00009a002

  日期：1995.4