2,3-Butanediol, 1,4-dibromo-, diacetate, (R,R)- | 2691-17-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-Butanediol, 1,4-dibromo-, diacetate, (R,R)-
• 英文别名: [(2R,3R)-3-acetyloxy-1,4-dibromobutan-2-yl] acetate
• CAS: 2691-17-0；2691-18-1；78314-10-0；128730-80-3
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: DANAEPFRHWNMKW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-Butanediol, 1,4-dibromo-, diacetate, (R,R)- 在 sodium sulfide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以95%的产率得到2,3-di-O-acetyl-1,4-dideoxy-1,4-thio-D,L-threitol
  参考文献：
  名称：

  Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives

  摘要：

  Polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane rings have been readily obtained in excellent yields (78-95%) from thioheterocyclisation of the bielectrophilic petacetylated alpha,omega -dibrominated derivatives of tetritols (erythritol (1) and D,L-threitol (4)), pentitols: (xylitol (7), ribitol (10) and D-arabinitol (14)) and hexitols (D-mannitol (17) and D-glucitol (20)), respectively. With 2,3,4,5-tetra-O-acetyl-1,6-dibromo-1,6-dideoxy-D-glucitol (21) as substrate, the unexpected 2,6-anhydro derivative 25 was obtained. This could be attributed to previous S-= regioselective nucleophilic attack at C-1 position followed by 1,2-transesterification and 2,6-O-heterocyclisation. The preferential attack at C-1 of the D-glucitol derivative 21 subsequently allowed a facile direct synthesis in good yields of 2,3,4,5,6-penta-O-acetyl-1-bromo-1-deoxy-D-glucitol (26), 2,3,4,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiobutyl-1-deoxy-D-glucitol (28) and 2,3,3,5-tetra-O-acetyl-6-bromo-6-deoxy-1-thiooctyl-1-deoxy-D-glucitol (28). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00442-7
• 作为产物：
  描述：

  sodium acetate 、 乙酸酐 在 乙酰溴 、 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以86%的产率得到2,3-Butanediol, 1,4-dibromo-, diacetate, (R,R)-
  参考文献：
  名称：

  Expedious synthesis of polyhydroxylated selena and thia-heterocycles via Se and S-ring closure of α,ω-dibromoalditols

  摘要：

  The selena and thiaanhydro alditols (with xylo, ribo, D-arabino, erythro, D,L-threo and D-manno configuration) were easily and expeditiously synthesized in good to excellent yields by reaction of selenure and sulfur ions as binucleophiles with alpha,omega-dibromoalditols as bis-electrophilic substrates. With the 1,6-dibromo-D-glucitol derivative as substrate, only the corresponding thiepane derivative was obtained while the selenaheterocyclistation attempte led to complex mixture. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.061

文献信息

• Synthesis of α,ω‐Diazidoalditol Derivatives via Both <i>bis</i>‐ or <i>tris</i>‐Cyclic Sulfites and Peracetylated α,ω‐Dibromoalditols as Bielectrophilic Intermediates
  作者：Virginie Glaçon、Mohammed Benazza、Aniss El Anzi、Daniel Beaupère、Gilles Demailly

  DOI：10.1081/car-120030470

  日期：2004.12.26

  The alpha,omega-diazidoalditol derivatives with erythro, threo, xylo, ribo, D-arabino, D-manno, and D-gluco configuration were efficiently synthesized, respectively, from bis- or tris-cyclic sulfite or peracetylated alpha,omega-dibromoalditol intermediates. The cyclic sulfite intermediates has the advantage to lead directly to the free alpha,omega-diazido-alpha,omega-dideoxyalditols.
• 710. The preparation of αω-di-O-methanesulphonyl derivatives of some sugar alcohols
  作者：Stanley S. Brown、G. M. Timmis

  DOI：10.1039/jr9610003656

  日期：——
• Alditol thiacrowns via a ring-closing metathesis of carbohydrate-derived α,ω-dithioallylethers
  作者：Mohammed Benazza、Alain Danquigny、Guy Novogrocki、Luca Valgimigli、Riccardo Amorati、Fiammetta Ferroni、Catherine Demailly-Mullie、Aloysius Siriwardena、David Lesur、Frédérick Aubry、Gilles Demailly

  DOI：10.1016/j.tet.2015.06.049

  日期：2015.8

  We report a newly developed synthesis of a number of alditol thiacrowns using an eco-friendly and versatile two-step strategy: the regioselective thioallyletherification of a polyhydroxylated alditol followed by a ring closing metathesis using the Grubbs second generation catalyst. This approach allows a series of target thiacrown products to be obtained in acceptable to good yields, from the corresponding alpha-omega-dithioallylether alditol starting materials featuring either the xylo, ribo, threo, erythro, D-manno or D-gluco configurations. The per-O-acetylated D-mannitol dithioallyether 10, easily obtained on a large scale using this approach, was selected for evaluation as both an antibacterial and an antioxidant Although no antibacterial activity was observed for the bacterial strains investigated, compound 10 is shown to be an antioxidant, and able to quench hydrogen peroxide in a stoichiometric fashion. (C) 2015 Elsevier Ltd. All rights reserved.
• Prochazka,M., Collection of Czechoslovak Chemical Communications, 1965, vol. 30, p. 1158 - 1168
  作者：Prochazka,M.

  DOI：——

  日期：——