meso-2,3-diacetoxy-1,4-dibromobutane | 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: meso-2,3-diacetoxy-1,4-dibromobutane
• 英文别名: (+/-)-1,4-Dibrom-2,3-diacetoxy-butan；meso-1,4-Dibrom-2,3-diacetoxy-butan；2,3-Butanediol, 1,4-dibromo-, diacetate, (theta,S)-；[(2S,3R)-3-acetyloxy-1,4-dibromobutan-2-yl] acetate
• CAS: 2691-17-0
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: DANAEPFRHWNMKW-OCAPTIKFSA-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：

  meso-2,3-diacetoxy-1,4-dibromobutane 在 sodium sulfide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.08h， 生成 2,3-di-O-acetyl-1,4-dideoxy-1,4-thioerythritol
  参考文献：
  名称：

  通过环硫代碳酸酯作为中间体，可合成某些糖醇或糖衍生物的单或双烯丙基卤代硫醇碳酸盐。

  摘要：

  我们在本文中描述了通过与通常使用的烯丙基卤而不是甲基碘反应，经由环状硫代碳酸酯官能团扩展1,2或1,3-二醇的卤化。这项研究是在常规加热和无微波溶剂的条件下，使用某些糖醇，硫代脱水醛糖醇和醛糖衍生物成功进行的。

  DOI：

  10.1016/j.carres.2009.11.018
• 作为产物：
  描述：

  Acetic acid (1S,2S)-2-acetoxy-3-amino-1-bromomethyl-propyl ester; hydrobromide 在 氢溴酸 、 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 meso-2,3-diacetoxy-1,4-dibromobutane
  参考文献：
  名称：

  Selective action of acetylating agents on 1-amino-1-deoxy-D-erythritol and its derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(00)80357-2

文献信息

• Influence of the methyl group in isoprene epoxides on reactivity compared to butadiene epoxides: Biological significance
  作者：Bernard T. Golding、Manuel Abelairas-Edesa、Rowena D. Tilbury、Joanne P. Wilson、Daping Zhang、Alistair P. Henderson、Christine Bleasdale、William Clegg、William P. Watson

  DOI：10.1016/j.cbi.2022.109949

  日期：2022.7

  mixture of 1:1 [methyl 2-(3,4-dihydroxy-3-methylpyrrolidin-1-yl)-3-methylbutanoates] and 2:1 adducts. Meso-2,2′-bioxirane reacted with N-acetylcysteine methyl ester in methanol to afford meso-thiolane-3,4-diol, by elimination of N-acetyldehydroalanine methyl ester from a precursor cyclic adduct. Similarly, 2-methyl-2,2′-bioxirane gave solely 3-methylthiolane-3,4-diols. Thus, the methyl group of isoprene

  已经比较了 1,3-丁二烯和异戊二烯 (2-甲基-1,3-丁二烯) 的环氧化物与氧、氮和硫亲核试剂的反应，以便更好地了解这些环氧化物对人体的相对毒性。rac的水解。在( 18 O)水中的-乙烯基环氧乙烷得到77% (2- 18 O)but-3-ene-1,2-二醇和23% (1- 18 O)but-3-ene-1,2-二醇。来自 ( S )-乙烯基环氧乙烷水解的丁-3-烯-1,2-二醇的R : S比为75:25。因此，乙烯基环氧乙烷的水解是通过以 3:1 的比例在 C-2 和 C-3 上竞争 S N 2 攻击而发生的，没有 S N 1 组分。rac的水解。-2-乙烯基-2-甲基环氧乙烷得到 2-羟基-2-甲基丁-3-烯-1-醇 (73%) 和 27% 的4-羟基-和Z-异构体的 2:1 混合物2-甲基丁-2-烯-1-醇。在( 18 O)水中获得(2- 18 O)2-羟基-2-甲基丁-3-烯-1-醇。这些产物的形成是通过
• 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.
• Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives
  作者：Sami Halila、Mohammed Benazza、Gilles Demailly

  DOI：10.1016/s0040-4039(01)00442-7

  日期：2001.5

  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.
• Expedious synthesis of polyhydroxylated selena and thia-heterocycles via Se and S-ring closure of α,ω-dibromoalditols
  作者：Mohammed Benazza、Sami Halila、Camille Viot、Alain Danquigny、Christèle Pierru、Gilles Demailly

  DOI：10.1016/j.tet.2004.01.061

  日期：2004.3

  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.
• 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.