(3R,4R,5S)-5-(溴甲基)-3,4-二羟基二氢-2(3H)-呋喃酮 | 191348-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R,4R,5S)-5-(溴甲基)-3,4-二羟基二氢-2(3H)-呋喃酮
• 英文名称: 5-bromo-5-deoxy-D-xylono-1,4-lactone
• 英文别名: (3R,4R,5S)-5-(Bromomethyl)-3,4-dihydroxydihydrofuran-2(3H)-one；(3R,4R,5S)-5-(bromomethyl)-3,4-dihydroxyoxolan-2-one
• CAS: 191348-58-0
• 化学式: C₅H₇BrO₄
• 分子量: 211.012
• InChiKey: MYRODPRKOYUJTI-FLRLBIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-5-(溴甲基)-3,4-二羟基二氢-2(3H)-呋喃酮 在 sodium tetrahydroborate 、 叠氮化锂 、 Amberlite IR-120H⁺ 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-azido-1-deoxy-L-xylitol
  参考文献：
  名称：

  Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected d-pentono-1,4-lactones

  摘要：

  The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.

  DOI：

  10.1016/s0008-6215(99)00261-x
• 作为产物：
  描述：

  D-木糖酸-gamma-内酯 在 二溴亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到(3R,4R,5S)-5-(溴甲基)-3,4-二羟基二氢-2(3H)-呋喃酮
  参考文献：
  名称：

  Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives

  摘要：

  Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00044-x

文献信息

• Influence of alkyl chain length on the mesomorphism of 5-S-alkyl-5-thiopentonolactones and 5-S-alkyl-5-thiopentitols
  作者：Imane Stasik、Sébastien Gottis、Céline Falentin-Daudré、Claire Meyer

  DOI：10.1016/j.carres.2014.04.008

  日期：2014.6

  (d-ribono, d-arabinono and d-xylono) and corresponding alditol derivatives with the general formula Su-SR (R=CnH2n+1; n=5-12) are studied. It was shown that the thermotropic and lyotropic phase transition temperatures are influenced by the following structural parameters: alkyl chain length, cyclic or acyclic Su structure and alditol conformation. Besides, it seems that n parity affects thermotropic

  研究了S-烷硫基戊内酯（d-核糖基，d-阿拉伯糖基和d-木糖基）和相应的通式为Su-SR（R = CnH2n + 1； n = 5-12）的糖醇衍生物的介晶性质。结果表明，热致相变温度受以下结构参数的影响：烷基链长，环状或无环Su结构和糖醇构象。此外，似乎n平价会影响热致相变温度。
• An efficient and facile three-step synthesis of 5-amino-5-deoxy-D-pentonolactams from unprotected D-pentono-1,4-lactones.
  作者：Véronique Bouchez、Imane Stasik、Daniel Beaupère、Raoul Uzan

  DOI：10.1016/s0040-4039(97)10065-x

  日期：1997.11

  Regioselective bromination of D-pentono-1,4-lactones with SOBr2 in DMF led to 5-bromo-5-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 5-amino-5-deoxy-D-pentonolactams in 60-83% overall yield. (C) 1997 Elsevier Science Ltd.
• Efficient syntheses of 1-S-alkyl-1-thio-l-ribitols, d-lyxitols and l-xylitols from d-pentono-1,4-lactones
  作者：Jérôme Lalot、Gaëtane Manier、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/s0008-6215(01)00204-x

  日期：2001.9

  The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, and D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolated in good yields (82-95%). Reduction with NaBH4 of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives
  作者：Véronique Bouchez、Imane Stasik、Daniel Beaupère、Raoul Uzan

  DOI：10.1016/s0008-6215(97)00044-x

  日期：1997.5

  Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds. (C) 1997 Elsevier Science Ltd.
• Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected d-pentono-1,4-lactones
  作者：Véronique Bouchez、Imane Stasik、Daniel Beaupère

  DOI：10.1016/s0008-6215(99)00261-x

  日期：1999.1

  The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.