5-bromo-5-deoxy-D-ribono-1,4-lactone | 160456-85-9

• 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-ribono-1,4-lactone
• 英文别名: (3R,4S,5S)-5-(bromomethyl)-3,4-dihydroxyoxolan-2-one
• CAS: 160456-85-9
• 化学式: C₅H₇BrO₄
• 分子量: 211.012
• InChiKey: MYRODPRKOYUJTI-BXXZVTAOSA-N

物化性质

• 沸点：
  355.5±11.0 °C(Predicted)
• 密度：
  2.019±0.06 g/cm3(Predicted)

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-ribono-1,4-lactone 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-ribitol
  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-(+)-核糖酸-1,4-内酯 在 二溴亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到5-bromo-5-deoxy-D-ribono-1,4-lactone
  参考文献：
  名称：

  First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

  摘要：

  首次合成2,3,4-三-O-苄基-5-硫代-d-甘露糖内酯，通过五个步骤从5-溴-5-去氧-d-甘露糖-1,4-内酯起始合成。对甲基2,3,4-三-O-苄基-5-溴-5-去氧-d-核糖酸酯（7）的溴化物基团的取代，获得了96%产率的甲基2,3,4-三-O-苄基-5-S-乙酰-5-硫代-d-核糖酸酯（10）。化合物10的皂化反应生成了98%产率的甲基2,3,4-三-O-苄基-5-硫代-d-甘露酸（11）。用DIC-HOBt作为偶联试剂处理11，经过环化后得到目标化合物2,3,4-三-O-苄基-5-硫代-d-甘露糖内酯（12），产率为75%。

  DOI：

  10.1055/s-2005-872079

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。
• Efficient synthesis of new N-alkyl-d-ribono-1,5-lactams from d-ribono-1,4-lactone
  作者：Céline Falentin、Daniel Beaupère、Gilles Demailly、Imane Stasik

  DOI：10.1016/j.tetlet.2009.07.026

  日期：2009.9

  d-Ribono-1,4-lactone was treated with ethylamine in DMF to afford N-ethyl-d-ribonamide 9a in quantitative yield. Bromination of amide 9a by the system SOBr2 in DMF or PPh3/CBr4 in pyridine led, after acetylation, to epoxide 7. However, treatment of amide 9a with acetyl bromide in dioxane followed by acetylation gave 2,3,4-tri-O-acetyl-5-bromo-5-deoxyl-N-ethyl-d-ribonamide 10a. Methanolysis of 10a, with

  d -Ribono -1,4-内酯与乙胺的DMF溶液处理，得到Ñ乙基d -ribonamide 9A，定量收率。乙酰化后，DMF中的SOBr 2或吡啶中的PPh 3 / CBr 4导致酰胺9a溴化，生成环氧化物7。然而，治疗酰胺9A与在二恶烷乙酰溴，然后乙酰化，得到2,3,4-三ø -乙酰基-5-溴-5- deoxyl -N -乙基- d -ribonamide 10A。用甲醇钠将10a甲醇分解，得到N乙基d -ribonolactam 11A在51％的总产率。使用这种方法，Ñ丁基，Ñ -己基，Ñ十二烷基，和Ñ苄基d -ribonolactams 11B - ë是在良好的产率（48-53％）获得。
• 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，
• Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone
  作者：Céline Falentin-Daudre、Daniel Beaupère、Imane Stasik-Boutbaiba

  DOI：10.1016/j.carres.2010.07.005

  日期：2010.9

  N-(3-methyl-pyridinyl)-, N-(2-hydroxy-ethyl)-, and N-(2-cyano-ethyl)-d-ribonamides 8b-h were obtained in quantitative yield. Bromination of the amides 8a-e with acetyl bromide in dioxane followed by acetylation gave 2,3,4-tri-O-acetyl-5-bromo-5-deoxy-N-ethyl, N-butyl, N-hexyl, N-dodecyl, and N-benzyl-d-ribonamides 9a-e in 40-54% yields. To obtain 2,3,4-tri-O-acetyl-5-bromo-5-deoxy-N-(3-methyl-pyridinyl)-, N-(2-hydroxy-ethyl)-

  用乙胺在DMF中处理d-核糖-1，4-内酯，以定量收率得到N-乙基-d-核糖酰胺8a。使用该反应步骤，N-丁基，N-己基，N-十二烷基，N-苄基，N-（3-甲基-吡啶基）-，N-（2-羟基-乙基）-和N-（2-氰基）以定量产率获得了-乙基）-d-核糖酰胺8b-h。在二恶烷中用乙酰溴将酰胺8a-e溴化，然后乙酰化，得到2,3,4-三-O-乙酰基-5-溴-5-脱氧-N-乙基，N-丁基，N-己基，N-十二烷基和N-苄基-d-核糖酰胺9a-e，产率为40-54％。得到2,3,4-三-O-乙酰基-5-溴-5-脱氧-N-（3-甲基-吡啶基）-，N-（2-羟基-乙基）-和N-（2-氰基-乙基）-9f-h，在酰胺化反应之前必须进行溴化。在DMF中用NaH处理溴酰胺9a-h，然后进行甲醇分解，以定量收率得到N-烷基-d-核糖基-1,5-内酰胺12a-h。
• 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.