2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone | 164169-23-7

• 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: 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone
• 英文别名: [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4,5-dibromo-6-oxooxan-2-yl]methyl benzoate
• CAS: 164169-23-7
• 化学式: C₂₇H₂₀Br₂O₈
• 分子量: 632.259
• InChiKey: MFAADBWLVLDTJV-XAYSYOTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone 在 偶氮二异丁腈 吡啶 、 aluminum oxide 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 methyl 3-deoxy-2,4,6-tri-O-benzoyl-β-D-erythro-hex-2-ulofuranosonate
  参考文献：
  名称：

  3-脱氧-d-赤--2-己磺酸的呋喃糖衍生物及其3-溴和3-氘代类似物的合成

  摘要：

  2,4,6-三-O-苯甲酰基-2,3-二溴-3-脱氧-D-altrono-1,5-内酯的甲醇解反应生成甲基3-溴-3-脱氧-2,4,6-三甲基-O-苯甲酰基-α-D-ribo-hex-2-ulofuranosonate（3）和类似的4,6-二-O-苯甲酰基衍生物的异头混合物，不含HO-2。在2,2'-偶氮二异丁腈的存在下，用氢化三丁基锡和氘代三丁基锡对化合物3进行脱溴处理，分别得到3-脱氧-D-赤型-2-己磺酸及其相应的3-氘代类似物的相应衍生物。 。产物和中间体的结构通过光谱方法和化学转化来确定。

  DOI：

  10.1016/s0008-6215(00)00132-4
• 作为产物：
  描述：

  2,4,6-tri-O-benzoyl-3-deoxy-D-erythro-hex-2-enono-1,5-lactone 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以87%的产率得到2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrono-1,5-lactone
  参考文献：
  名称：

  Bromination of sugar enones and enonolactones

  摘要：

  Bromination of 2,4,6-tri-O-benzoyl-3-deoxy-D-erytro-hex-2-enono-1,5-lactone (1) took place diastereoselectively to afford a single product: 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrofio-1,5-lactone (2). The configuration of C-2 and C-3 was determined as R,R by NMR spectroscopy and taking into account considerations of the stereochemical course of the bromination. The configuration of 2 was confirmed by X-ray analysis, which also revealed that the conformation of the lactone ring consists of a H-4(3)(D) distorted half-chair. The bromine addition to 2,5,6,7-tetra-O-benzoyl-D-arabino-hept-2-enone-1,4-lactone (5), readily prepared by DBU-promoted elimination from the perbenzoylated lactone derivative 4, was also diastereoselective and led to the dibromo derivative 6, whose configuration for C-2 and C-3 was assigned as S,S. Bromination of the alpha,beta-unsaturated carbonyl system of 2-propyl 6-O-acetyl-3,4-dideoxy-alpha-oglycero-hex-3-enopyranosid-2-ulose (7) afforded an unsaturated monobromo derivative: 2-propyl 6-O-acetyl-3-bromo-3,4-dideoxy-alpha-D-glycero-hex-3-enopyranosid-2-ulose (8), suggesting that dehydrobromination occurred after addition of bromine.

  DOI：

  10.1016/0008-6215(94)00352-g

文献信息

• Synthesis of furanose derivatives of 3-deoxy-d-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs
  作者：Christián Di Nardo、Oscar Varela

  DOI：10.1016/s0008-6215(00)00132-4

  日期：2000.10

  the anomeric mixture of the analogous 4,6-di-O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2'-azo-bisisobutyronitrile affording, respectively, the corresponding derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and its 3-deuterio analog. The structure of the products and intermediates was established

  2,4,6-三-O-苯甲酰基-2,3-二溴-3-脱氧-D-altrono-1,5-内酯的甲醇解反应生成甲基3-溴-3-脱氧-2,4,6-三甲基-O-苯甲酰基-α-D-ribo-hex-2-ulofuranosonate（3）和类似的4,6-二-O-苯甲酰基衍生物的异头混合物，不含HO-2。在2,2'-偶氮二异丁腈的存在下，用氢化三丁基锡和氘代三丁基锡对化合物3进行脱溴处理，分别得到3-脱氧-D-赤型-2-己磺酸及其相应的3-氘代类似物的相应衍生物。 。产物和中间体的结构通过光谱方法和化学转化来确定。
• Bromination of sugar enones and enonolactones
  作者：Christían Di Nardo、Oscar Varela、Rosa M. de Lederkremer、Ricardo F. Baggio、Daniel R. Vega、María T. Garland

  DOI：10.1016/0008-6215(94)00352-g

  日期：1995.4

  Bromination of 2,4,6-tri-O-benzoyl-3-deoxy-D-erytro-hex-2-enono-1,5-lactone (1) took place diastereoselectively to afford a single product: 2,4,6-tri-O-benzoyl-2,3-dibromo-3-deoxy-D-altrofio-1,5-lactone (2). The configuration of C-2 and C-3 was determined as R,R by NMR spectroscopy and taking into account considerations of the stereochemical course of the bromination. The configuration of 2 was confirmed by X-ray analysis, which also revealed that the conformation of the lactone ring consists of a H-4(3)(D) distorted half-chair. The bromine addition to 2,5,6,7-tetra-O-benzoyl-D-arabino-hept-2-enone-1,4-lactone (5), readily prepared by DBU-promoted elimination from the perbenzoylated lactone derivative 4, was also diastereoselective and led to the dibromo derivative 6, whose configuration for C-2 and C-3 was assigned as S,S. Bromination of the alpha,beta-unsaturated carbonyl system of 2-propyl 6-O-acetyl-3,4-dideoxy-alpha-oglycero-hex-3-enopyranosid-2-ulose (7) afforded an unsaturated monobromo derivative: 2-propyl 6-O-acetyl-3-bromo-3,4-dideoxy-alpha-D-glycero-hex-3-enopyranosid-2-ulose (8), suggesting that dehydrobromination occurred after addition of bromine.