5-bromo-5-deoxy-D-arabinono-1,4-lactone | 82805-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-5-deoxy-D-arabinono-1,4-lactone
• 英文别名: (3S,4S,5S)-5-(bromomethyl)-3,4-dihydroxyoxolan-2-one
• CAS: 82805-13-8
• 化学式: C₅H₇BrO₄
• 分子量: 211.012
• InChiKey: MYRODPRKOYUJTI-JJYYJPOSSA-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：

  5-bromo-5-deoxy-D-arabinono-1,4-lactone 在 palladium on activated charcoal sodium tetrahydroborate 、 叠氮化锂 、 Amberlite IR-120H⁺ 、 ammonium formate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-amino-1-deoxy-D-lyxitol
  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：

  potassium 4-keto-D-arabonate 在 依沙酰胺 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以26%的产率得到5-bromo-5-deoxy-D-arabinono-1,4-lactone
  参考文献：
  名称：

  The preparation of some bromodeoxy- and dibromodideoxy-pentonolactones

  摘要：

  DOI：

  10.1016/s0008-6215(00)82222-3

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。
• Deoxyiminoalditols from aldonolactones — V. Preparation of the four stereoisomers of 1,5-dideoxy-1,5-iminopentitols. Evaluation of these iminopentitols and three 1,5-dideoxy-1,5-iminoheptitols as glycosidase inhibitors
  作者：Michael Godskesen、Inge Lundt、Robert Madsen、Bryan Winchester

  DOI：10.1016/s0968-0896(96)00167-8

  日期：1996.11

  synthesized. The corresponding aldonolactones (1, 7 and 11) or aldonic acid ester (15b) having a leaving group at C-5 gave by reaction with aqueous ammonia, the 5-amino-5-deoxy-1,5-lactams, 2, 8, 12 and 17, respectively. Reduction of the lactam function using sodium borohydride/acetic or trifluoroacetic acid, or borane dimethyl sulfide complex yielded the iminopentitols. The compounds 3, 9, 13 and 18, together

  四种立体异构体1,5-二脱氧-1,5-亚氨基戊醇与D-阿拉伯糖（-D-lyxo-）（3），ribo-（9），L-lyxo（L-阿拉伯糖-）（13）和xylo （18）合成了构型。通过与氨水反应生成相应的C-5上具有离去基团的醛内酯（1、7和11）或醛糖酸酯（15b），5-氨基-5-脱氧-1,5-内酰胺2、2、8 ，12和17。使用硼氢化钠/乙酸或三氟乙酸或硼烷二甲基硫醚络合物降低内酰胺功能，得到亚氨基戊糖醇。测试了化合物3、9、13和18以及三种1,5-二脱氧-1,5-亚氨基庚糖醇19,20和21对人肝提取物中糖苷酶活性的抑制作用。化合物18是有效的β-葡萄糖苷酶抑制剂，化合物19是中等良好的β-葡萄糖苷酶抑制剂。化合物3与19、20和21一起，
• 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.