4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide | 136465-97-9

• 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: 4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide
• 英文别名: 4(S)-[1(S)-azido-2-phenylethyl]-1,3,2-dioxathiolane 2,2-dioxide；(4S)-4-[(1S)-1-azido-2-phenylethyl]-1,3,2-dioxathiolane 2,2-dioxide
• CAS: 136465-97-9
• 化学式: C₁₀H₁₁N₃O₄S
• 分子量: 269.281
• InChiKey: QBHWRFJQFRFYNJ-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide 在 palladium on activated charcoal N-乙基吗啉 、 硫酸 、 氢气 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 124.0h， 生成 沙喹那韦
  参考文献：
  名称：

  Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

  摘要：

  Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation. The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1. Kilogram quantities of Ro 31-8959 have been prepared using this route.

  DOI：

  10.1021/jo00092a026
• 作为产物：
  描述：

  (2S,3S)-2-azido-1-phenyl-butane-3,4-diol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 4(S)-(1(S)-Azido-2-phenylethyl)-1,3,2-dioxathiolane 2,2-dioxide
  参考文献：
  名称：

  Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959

  摘要：

  Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials. Six approaches for the large-scale synthesis of this compound have been studied. All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5. They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation. The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1. Kilogram quantities of Ro 31-8959 have been prepared using this route.

  DOI：

  10.1021/jo00092a026

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。
• J. Org. Chem. 1994, 59, 3656-3664
  作者：

  DOI：——

  日期：——
• MACROCYCLIC LACTAM PROKINETIC AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP0579770B1

  公开（公告）日：1996-06-26
• US5451678A
  申请人：——

  公开号：US5451678A

  公开（公告）日：1995-09-19