5-bromo-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose | 42854-94-4

• 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-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 5-bromo-O¹,O²-isopropylidene-α-D-5-deoxy-xylofuranose；5-Bromo-5-deoxy-1,2-O-(1-methylethylidene)pentofuranose；(3aR,5S,6R,6aR)-5-(bromomethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 42854-94-4
• 化学式: C₈H₁₃BrO₄
• 分子量: 253.093
• InChiKey: YKNQRVLADQAQIT-XZBKPIIZSA-N

物化性质

• 沸点：
  335.9±37.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 镍 氢气 、 氢气 作用下， 生成 5-deoxy-D-xylofuranose
  参考文献：
  名称：

  Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives

  摘要：

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00255-3
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 生成 5-bromo-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Ni催化醇与芳基卤化物的正式交叉电子偶联

  摘要：

  未活化醇的直接偶联仍然是当前合成化学中的一个挑战。我们在此展示了一种建立在醇与芳基卤化物的原位卤化/还原偶联以形成 Csp 2 -Csp 3键的策略。2-氯-3-乙基苯并[ d ]恶唑-3-鎓盐 (CEBO) 和 TBAB 作为温和溴化试剂的组合能够在 CH 3 中在一到 5 分钟内将范围广泛的醇快速转化为其溴化物对应物CN 和 DMF，在化学还原剂存在下与 Ni 催化的交叉亲电偶联条件相容。本方法适用于无数结构复杂的醇的芳基化，而无需制备卤代烷。更重要的是，温和且动力学快速的溴化过程在对称二醇的溴化/芳基化和多元醇中较少的空间位阻羟基中显示出良好的选择性，从而为二醇和多元醇的选择性官能化提供了希望，而无需费力的保护/脱保护操作。这项工作的实用性在许多碳水化合物、药物化合物和天然醇的芳基化中也很明显。

  DOI：

  10.1021/acscatal.1c04239

文献信息

• Bicyclic azasugars containing a glycosidic heteroatom: D-xylose analogues
  作者：David A. Berges、Jianmei Fan、Sylvie Devinck、Nannan Liu、N. Kent Dalley

  DOI：10.1016/s0040-4020(99)00335-x

  日期：1999.5

  Bicyclic azasugar analogues of D-xylose containing a glycosidic heteroatom have been prepared and characterized by X-ray crystallography and NMR spectroscopy. Compounds in which the glycosidic heteroatom is N (substituted with H or CH3), O, and S have been prepared, and the ring fused to the azasugar ring has been 5- or 6-membered; 7-membered analogues are either unstable or do not form. alpha-Anomers are present when the glycosidic heteroatom is O or S but not N, and even then they are less favored than the corresponding beta-anomers. (C) 1999 Elsevier Science Ltd. All rights reserved.
• D-xylofuranose: Conversion to its' 3,5-oxetane via an unusual reductive displacement of phthalimide and subsequent regioselective ring opening.
  作者：Nigel G. Cooke、D.Alan Jones、Andrew Whiting

  DOI：10.1016/s0040-4020(01)88323-x

  日期：1992.1

  3,5-anhydro-1,2-O-isopropylidene-alpha-D-xylofuranose has been prepared from the corresponding 5-phthalimido derivative in quantitative yield, and its' formation involves an unusual phthalimide substitution in the presence of sodium borohydride in methanol. A mechanism is proposed for this unusual cyclisation, which involves initial activation of the phthalimide. Subsequent Lewis-acid catalysed ring openings have been achieved in a regiospecific manner.
• Synthesis and stereochemistry of telomers of vinylene carbonate as synthetic intermediates for carbohydrates
  作者：Toshinari Tamura、Takehisa Kunieda、Takeo Takizawa

  DOI：10.1021/jo00915a007

  日期：1974.1
• Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
  作者：Quan Lin、Guobin Ma、Hegui Gong

  DOI：10.1021/acscatal.1c04239

  日期：2021.11.19

  and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation

  未活化醇的直接偶联仍然是当前合成化学中的一个挑战。我们在此展示了一种建立在醇与芳基卤化物的原位卤化/还原偶联以形成 Csp 2 -Csp 3键的策略。2-氯-3-乙基苯并[ d ]恶唑-3-鎓盐 (CEBO) 和 TBAB 作为温和溴化试剂的组合能够在 CH 3 中在一到 5 分钟内将范围广泛的醇快速转化为其溴化物对应物CN 和 DMF，在化学还原剂存在下与 Ni 催化的交叉亲电偶联条件相容。本方法适用于无数结构复杂的醇的芳基化，而无需制备卤代烷。更重要的是，温和且动力学快速的溴化过程在对称二醇的溴化/芳基化和多元醇中较少的空间位阻羟基中显示出良好的选择性，从而为二醇和多元醇的选择性官能化提供了希望，而无需费力的保护/脱保护操作。这项工作的实用性在许多碳水化合物、药物化合物和天然醇的芳基化中也很明显。
• Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives
  作者：Philipp Hadwiger、Peter Mayr、Andreas Tauss、Arnold E Stütz、Bernd Nidetzky

  DOI：10.1016/s0960-894x(99)00255-3

  日期：1999.6

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.