2,4,6-tri-O-bemzoyl-3-deoxy-D-arabino-hexono-1,5-lactone | 53942-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tri-O-bemzoyl-3-deoxy-D-arabino-hexono-1,5-lactone
• 英文别名: 2,4,6-tri-O-benzoyl-3-deoxy-D-arabino-hexono-1,5-lactone；2,4,6-tri-O-benzoyl-3-deoxy-D-arabino-1,5-lactone；2,4,6-Tri-O-benzoyl-3-desoxy-D-arabino-hexono-1,5-lacton；2,4,6-Tri-O-benzoyl-3-deoxy-D-arabino-hexono-1,5-lacton；[(2R,3S,5S)-3,5-dibenzoyloxy-6-oxooxan-2-yl]methyl benzoate
• CAS: 53942-34-0
• 化学式: C₂₇H₂₂O₈
• 分子量: 474.467
• InChiKey: GQTDWXHFBGGVKK-RJGXRXQPSA-N

物化性质

• 熔点：
  154-156 °C(Solv: acetone (67-64-1))
• 沸点：
  600.6±44.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 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-bemzoyl-3-deoxy-D-arabino-hexono-1,5-lactone 在 吡啶 、 sodium methylate 、 二(3-甲基丁烷-2-基)硼烷 作用下， 以 吡啶 为溶剂， 反应 8.0h， 生成 1-O-acetyl-2,5,6-tri-O-benzoyl-3-deoxy-a-D-arabino-hexaforanose
  参考文献：
  名称：

  3-脱氧-d-阿拉伯糖基己糖的结晶呋喃糖衍生物：核磁共振波谱法的构象研究

  摘要：

  摘要2,4,6-三-O-苯甲酰基-3-脱氧-d-阿拉伯糖的脱苯甲酰-己烯-1,5-内酯（1），然后真空加热并再苯甲酰化，得到2,5,6-三-O -苯甲酰基-3-脱氧-d-阿拉伯糖-己烯-1,4-内酯（2）。用二亚氨基硼烷还原2得到2,5,6-三-O-苯甲酰基-3-脱氧-d-阿拉伯糖-六呋喃糖（3），一种方便的呋喃糖衍生物，用于合成糖苷。用乙酸酐-吡啶将3乙酰化，得到1-O-乙酰基-2,5,6-三-O-苯甲酰基-3-脱氧-α-d-阿拉伯糖-六呋喃糖（4）。通过用溴代三甲基硅烷，然后用甲醇处理4得到的溴化物，将化合物4转化为甲基2,4,6-三-O-苯甲酰基-3-脱氧-α-d-阿拉伯糖-六呋喃糖苷（5）。5的脱苯甲酰化得到甲基3-脱氧-α-d-阿拉伯糖-六呋喃糖苷（6）。提及的所有化合物均以结晶形式获得。通过1 Hn.mr光谱（DAERM方法）对4、5和6进行了构象研究，并将13 Cn.mr光谱

  DOI：

  10.1016/0008-6215(85)90005-9
• 作为产物：
  描述：

  2,4,6-tri-O-benzoyl-3-deoxy-D-erythro-hex-2-enono-1,5-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以1.74 g的产率得到2,4,6-tri-O-bemzoyl-3-deoxy-D-arabino-hexono-1,5-lactone
  参考文献：
  名称：

  Factors influencing conformational preference and equilibria in solutions of aldono-1,5-lactones

  摘要：

  DOI：

  10.1016/0008-6215(87)80189-1

文献信息

• Highly stereoselective couplings of carbohydrate lactones with terpene ketones promoted by SmI2
  作者：Eric J. Enholm、Shujun Jiang

  DOI：10.1016/s0040-4039(00)60008-4

  日期：1992.10

  Lactone 3-deoxycarbohydrates were reacted with samarium diiodide (SmI2) in THF/HMPA and the terpene ketones, (−)-menthone or (+)-dihydrocarvone; a serial reductive deoxygenation and an attendant carbonyl addition reaction afforded C2 branched sugars with high diastereoselectivities (up to 99:1).

  使内酯3-脱氧碳水化合物与二碘化sa（SmI 2）在THF / HMPA中和萜烯酮（-）-薄荷酮或（+）-二氢香芹酮反应; 连续的还原性脱氧和伴随的羰基加成反应得到具有高非对映选择性（高达99∶1）的C 2支链糖。
• Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction
  作者：Eric J. Enholm、Shujun Jiang、Khalil Abboud

  DOI：10.1021/jo00067a045

  日期：1993.7

  A new deoxygenation-carbonyl addition reaction mediated by samarium(II) iodide (SmI2) in THF/HMPA was examined with carbohydrate lactones and several substrates containing an alpha-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex optically active carbohydrate lactones appended to terpene ketones. Simple esters smoothly afforded beta-hydroxy carbonyl products. Fully benzoate-protected 3-deoxycarbohydrate lactones were reacted with simple ketones to produce C2-branched sugars. The attendant carbonyl addition to the least sterically hindered face of the aldonolactone provided the major products. Moderate diastereoselectivities (up to 5:1) were observed in the simple ketone products as determined by difference NOE studies. Finally, the terpene ketones, (-)-menthone or (+)-dihydrocarvone, were coupled to 3-deoxycarbohydrate lactones which gave C2-branched sugars with very high diastereoselectivities (up to 99:1).
• Enholm, Eric J.; Jiang, Shujun, Heterocycles, 1992, vol. 34, # 12, p. 2247 - 2252
  作者：Enholm, Eric J.、Jiang, Shujun

  DOI：——

  日期：——
• NELSON, CHARLES R., CARBOHYDR. RES., 163,(1987) N 2, 275-278
  作者：NELSON, CHARLES R.

  DOI：——

  日期：——
• Crystalline furanose derivatives of 3-deoxy-d-arabino-hexose: Conformational studies by n.m.r. spectroscopy
  作者：Cecile du Mortier、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(85)90005-9

  日期：1985.6

  -benzoyl-3-deoxy-α- d - arabino -hexofuranose ( 4 ). Compound 4 was converted into methyl 2,4,6-tri- O -benzoyl-3-deoxy-α- d - arabino -hexofuranoside ( 5 ) through the bromide obtained by treatment of 4 with bromotrimethylsilane, followed by methanol. Debenzoylation of 5 gave methyl 3-deoxy-α- d - arabino -hexofuranoside ( 6 ). All compounds mentioned were obtained crystalline. Conformational studies of 4, 5, and

  摘要2,4,6-三-O-苯甲酰基-3-脱氧-d-阿拉伯糖的脱苯甲酰-己烯-1,5-内酯（1），然后真空加热并再苯甲酰化，得到2,5,6-三-O -苯甲酰基-3-脱氧-d-阿拉伯糖-己烯-1,4-内酯（2）。用二亚氨基硼烷还原2得到2,5,6-三-O-苯甲酰基-3-脱氧-d-阿拉伯糖-六呋喃糖（3），一种方便的呋喃糖衍生物，用于合成糖苷。用乙酸酐-吡啶将3乙酰化，得到1-O-乙酰基-2,5,6-三-O-苯甲酰基-3-脱氧-α-d-阿拉伯糖-六呋喃糖（4）。通过用溴代三甲基硅烷，然后用甲醇处理4得到的溴化物，将化合物4转化为甲基2,4,6-三-O-苯甲酰基-3-脱氧-α-d-阿拉伯糖-六呋喃糖苷（5）。5的脱苯甲酰化得到甲基3-脱氧-α-d-阿拉伯糖-六呋喃糖苷（6）。提及的所有化合物均以结晶形式获得。通过1 Hn.mr光谱（DAERM方法）对4、5和6进行了构象研究，并将13 Cn.mr光谱