(2R,3R,4S,5S)-5-(Benzyloxy)-2-(hydroxymethyl)piperidine-3,4-diol | 1051942-01-8

• 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: (2R,3R,4S,5S)-5-(Benzyloxy)-2-(hydroxymethyl)piperidine-3,4-diol
• 英文别名: (2R,3R,4S,5S)-2-(hydroxymethyl)-5-phenylmethoxypiperidine-3,4-diol
• CAS: 1051942-01-8
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: UPEUPHIIBCRMSX-YVECIDJPSA-N

物化性质

• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S)-5-(Benzyloxy)-2-(hydroxymethyl)piperidine-3,4-diol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以53%的产率得到1-脱氧野尻霉素
  参考文献：
  名称：

  New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

  摘要：

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

  DOI：

  10.1021/ol8014495
• 作为产物：
  描述：

  (4S,5R)-4-((S)-2-azido-1-(benzyloxy)ethyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane 在 溶剂黄146 作用下， 反应 15.0h， 以33%的产率得到(3aR,4S,8S,8aR)-8-(Benzyloxy)-2,2-dimethylhexahydro-3aH-[1,3]dioxolo[4,5-d]azepin-4-ol
  参考文献：
  名称：

  New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition

  摘要：

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

  DOI：

  10.1021/ol8014495

文献信息

• USE OF $i(N)-SUBSTITUTED-1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL COMPOUNDS FOR TREATING HEPATITIS VIRUS INFECTIONS
  申请人：G.D. SEARLE & CO.

  公开号：EP1061922A1

  公开（公告）日：2000-12-27
• JP2002502875A
  申请人：——

  公开号：JP2002502875A

  公开（公告）日：2002-01-29
• [EN] USE OF N-SUBSTITUTED-1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL COMPOUNDS FOR TREATING HEPATITIS VIRUS INFECTIONS<br/>[FR] UTILISATION DE COMPOSES N-SUBSTITUE-1,5-DIDESOXY-1,5-IMINO-D-GLUCITOL DANS LE TRAITEMENT DES INFECTIONS DUES AU VIRUS DE L'HEPATITE
  申请人：G.D. SEARLE & CO.

  公开号：WO1999040916A1

  公开（公告）日：1999-08-19

  (EN) Provided are methods and compositions for treating hepatitis virus infections in mammals, especially humans. The methods comprise (1) administering $i(N)-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds alone or in combination with nucleoside antiviral agents, nucleotide antiviral agents, mixtures thereof, or immunomodulating/immunostimulating agents, or (2) administering $i(N)-substituted-1,5-dideoxy-1,5-imino-D-glucitol compounds alone or in combination with nucleoside antiviral agents, nucleotide antiviral agents, or mixtures thereof, and immunomodulating/immunostimulating agents.(FR) L'invention porte sur des procédés et des compositions utilisés dans le traitement des infections dues au virus de l'hépatite chez des mamifères, notamment chez l'homme. Ces procédés consistent à (1) administrer des composés $i(N)-substitué-1,5-didésoxy-1,5-imino-D-glucidol, seuls, ou en combinaison avec des agents antiviraux nucléosidiques, des agents antiviraux nucléotidiques, des mélanges de ceux-ci ou des agents immunomodulateurs/immunostimulateurs, ou (2) administrer des composés $i(N)-substitué-1,5-didésoxy-1,5-imino-D-glucidol, seuls, ou en combinaison avec des agents antiviraux nucléosidiques, des agents antiviraux nucléotidiques, des mélanges de ceux-ci et des agents immunomodulateurs/immunostimulateurs
• New Access to 1-Deoxynojirimycin Derivatives via Azide−Alkene Cycloaddition
  作者：Ying Zhou、Paul V. Murphy

  DOI：10.1021/ol8014495

  日期：2008.9.1

  The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-delta-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.