2,5,6,7-tetra-O-benzoyl-3-deoxy-D-arabino-hept-2-enono-1,4-lactone | 41356-09-6

• 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: 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-arabino-hept-2-enono-1,4-lactone
• 英文别名: [(2R,3S)-2,3-dibenzoyloxy-3-[(2R)-4-benzoyloxy-5-oxo-2H-furan-2-yl]propyl] benzoate
• CAS: 41356-09-6
• 化学式: C₃₅H₂₆O₁₀
• 分子量: 606.585
• InChiKey: ONVFZCNHIUWTBV-NNFJYWIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5,6,7-tetra-O-benzoyl-3-deoxy-D-arabino-hept-2-enono-1,4-lactone 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以47%的产率得到2,5,6,7-tetra-O-benzoyl-2,3-dibromo-3-deoxy-D-glycero-D-galacto-heptono-1,4-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
• 作为产物：
  描述：

  2,3,5,6,7-penta-O-benzoyl-D-glycero-D-gulo-heptono-1,4-lactone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以67%的产率得到2,5,6,7-tetra-O-benzoyl-3-deoxy-D-arabino-hept-2-enono-1,4-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

• β-elimination in aldonolactones. Synthesis of 2-deoxy-D-lyxo-hexose and 2-deoxy-D-arabino-hexose
  作者：Luis F. Sala、Alicia Fernández Cirelli、Rosa M. de Lederkremer

  DOI：10.1016/s0008-6215(00)83660-5

  日期：1980.1

  Abstract Benzoylation of D -glycero- L -manno-heptono-1,4-lactone (1) with benzoyl chloride and pyridine for 2 h afforded crystalline penta-O-benzoyl- D -glycero- L -manno-heptono-1,4-lactone (2), but a large excess of reagent during 8 h also led to 2,5,6,7-tetra-O- benzoyl-3-deoxy- D -lyxo-hept-2-enono-1,4-lactone (3). Catalytic hydrogenation of 3 was stereoselective and gave 2,5,6,7-tetra-O-benzoyl-3-deoxy-

  摘要用苯甲酰氯和吡啶将D-甘油-L-甘露聚糖-1,4-内酯（1）苯甲酰化2 h，得到结晶的五-O-苯甲酰基-D-甘油-L-甘露庚香-1,4 -内酯（2），但在8小时内试剂大量过量也导致生成2,5,6,7-四-O-苯甲酰基-3-脱氧-D -lyxo-hept-2-enono-1,4-内酯（3）。3的催化氢化是立体选择性的，得到2,5,6,7-四-O-苯甲酰基-3-脱氧-D-半乳糖-庚酮-1,4-内酯（4）。4的脱苯甲酰化，然后在硫酸水溶液中用硫酸铈进行氧化脱羧，得到2-脱氧-D-lyxo-己糖（5）。将相同的反应应用于3-脱氧-D-葡萄糖-庚基-1,4-内酯得到2-脱氧-D-阿拉伯糖基己糖（6）。
• 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.