2,4,6-tri-O-benzoyl-3-deoxy-D-erythro-hex-2-enono-1,5-lactone | 53942-33-9

• 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-3-deoxy-D-erythro-hex-2-enono-1,5-lactone
• 英文别名: [(2R,3S)-3,5-dibenzoyloxy-6-oxo-2,3-dihydropyran-2-yl]methyl benzoate
• CAS: 53942-33-9
• 化学式: C₂₇H₂₀O₈
• 分子量: 472.451
• InChiKey: NNTHQODOUBDQCG-JTHBVZDNSA-N

物化性质

• 沸点：
  592.6±43.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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-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
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 溴 、 sodium iodide 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 6.33h， 生成 2,4,6-tri-O-benzoyl-3-deoxy-D-erythro-hex-2-enono-1,5-lactone
  参考文献：
  名称：

  Ferrier, Robert J.; Tyler, Peter C., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2762 - 2766

  摘要：

  DOI：

文献信息

• Ready Conversion of Sugar Derived 5,6-Dihydro-2-pyrones into 3-Acyloxy- and 3-Acylamido-2-Pyrones
  作者：Alejandro Nin、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1055/s-1991-26383

  日期：——

  5-Acyloxy-6-acyloxymethyl-5,6-dihydro-2-pyrone derivatives (1a, b and 3b and 5-acyloxy-6-methyl-5,6-dihydro-2-pyrone (3a), obtained by acylation of 2-amino-2-deoxy-D-gluconic acid or L-rhamono- and D-glucono-1,5-lactones, react with tin(IV) chloride to give 3-acylamido- and 3-acyloxy-6-acyloxymethyl-2-pyrones (2a,b and 4b, respectively) and 3-benzoyloxy-6-methyl-2-pyrone (4a), in excellent yield. On prolonged reaction time (5h), the pyrone 4b underwent substitution of the allylic benzoate by chlorine to afford the corresponding 6-chloromethyl derivative 4c.

  5-酰氧基-6-酰氧甲基-5,6-二氢-2-吡喃酮衍生物（1a, b和3b）及5-酰氧基-6-甲基-5,6-二氢-2-吡喃酮（3a），通过对2-氨基-2-脱氧-D-葡糖酸或L-鼠李糖和D-葡糖-1,5-内酯的酰基化反应，和锡（IV）氯化物反应，生成3-酰胺基和3-酰氧基-6-酰氧甲基-2-吡喃酮（2a, b和4b，分别）以及3-苯甲氧基-6-甲基-2-吡喃酮（4a），产率极高。在延长反应时间（5小时）后，吡喃酮4b发生了通过氯取代烯丙基苯甲酸酯的反应，得到相应的6-氯甲基衍生物4c。
• Boron trifluoride-catalyzed oxidation of glycal esters: An effective and mild method for their conversion into α,β-unsaturated lactones
  作者：Pan Jarglis、Frieder W Lichtenthaler

  DOI：10.1016/s0040-4039(00)87705-9

  日期：1982.1

  An effective, one-step procedure for conversion of glycal and 2-acyloxyglycal esters to 2,3-unsaturated lactones has been developed, involving BF3-induced removal of the allylic acyloxy function and oxidation with m-chloroperbenzoic acid or pyridinium chlorochromate.

  已经开发出一种有效的一步法，将糖基和2-酰氧基糖基酯转化为2，3-不饱和内酯，包括BF 3诱导的烯丙基酰氧基官能团的去除和间氯过苯甲酸或氯代吡啶鎓铬酸盐的氧化。
• Lichtenthaler, Frieder W.; Roenninger, Stephan; Jarglis, Pan, Liebigs Annalen der Chemie, 1989, p. 1153 - 1162
  作者：Lichtenthaler, Frieder W.、Roenninger, Stephan、Jarglis, Pan

  DOI：——

  日期：——
• LICHTENTHALER, FRIEDER W.;RONNINGER, STEPHAN;JARGLIS, PAN, LIEBIGS ANN. CHEM.,(1989) N2, C. 1153-1161
  作者：LICHTENTHALER, FRIEDER W.、RONNINGER, STEPHAN、JARGLIS, PAN

  DOI：——

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

  DOI：——

  日期：——