2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone | 89950-76-5

• 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: 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4S)-4-benzoyloxy-3-hydroxy-5-oxooxolan-2-yl]ethyl] benzoate
• CAS: 89950-76-5
• 化学式: C₂₇H₂₂O₉
• 分子量: 490.466
• InChiKey: ZPIBPSLMUGIBEG-ACESQOTJSA-N

物化性质

• 沸点：
  637.7±55.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone 生成 3,5,6-tri-O-benzoyl-2-O-methyl-D-mannono-1,4-lactone
  参考文献：
  名称：

  JERONCIC, LUCIO O.;SZNAIDMAN, MARCOS L.;CIRELLI, ALICIA FERNANDEZ;LEDERKR+, CARBOHYDR. RES., 191,(1989) N, C. 130-137

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 、 D-甘露糖-1,4-内酯 在 吡啶 作用下， 反应 1.5h， 以70%的产率得到2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone
  参考文献：
  名称：

  The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp

  摘要：

  A convenient synthesis of free beta-D-Galf-(1 --> 3)-D-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose promoted by SnCl4, led to the B-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by alpha-D-Galp, we also synthesized 3-deoxy-beta D-xylo-hexofuranosyl-(1 --> 3)-D-Manp (8b) and p-nitrophenyl 3-deoxy-beta-D-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the beta-D-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00214-6

文献信息

• The use of aldonolactones for the synthesis of 2-O-methyl-l-rhamnose and 2-O-methyl-d-mannose
  作者：Lucio O. Jeroncic、Marcos L. Sznaidman、Alicia Fernandez Cirelli、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(89)85053-0

  日期：1989.8

  Synthese du O-methyl-2 L-rhamnose ou D-mannose a partir de la di-O-benzoyl-2,5 rhamnonolactone-1(4) et de la tri-O-benzoyl-2,5,6 mannonolactone-1(4) respectivement

  O-甲基-2 L-鼠李糖或D-甘露糖与二-O-苯甲酰-2,5鼠李糖内酯-1（4）和三-O-苯甲酰-2,5,6甘露内酯-1的合成（4）各别
• Facile Synthesis of per-<i>O-tert</i>-Butyldimethylsilyl-β-<scp>d</scp>-galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1021/jo8025274

  日期：2009.3.6

  The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4 beta) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly Of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.
• Gallo, Carola; Jeroncic, Lucio O.; Varela, Oscar, Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 841 - 852
  作者：Gallo, Carola、Jeroncic, Lucio O.、Varela, Oscar、Lederkremer, Rosa M. de

  DOI：——

  日期：——
• JERONCIC, LUCIO O.;SZNAIDMAN, MARCOS L.;CIRELLI, ALICIA FERNANDEZ;LEDERKR+, CARBOHYDR. RES., 191,(1989) N, C. 130-137
  作者：JERONCIC, LUCIO O.、SZNAIDMAN, MARCOS L.、CIRELLI, ALICIA FERNANDEZ、LEDERKR+

  DOI：——

  日期：——
• The glycosyl-aldonolactone approach for the synthesis of β-d-Galf-(1→3)-d-Manp and 3-deoxy-β-d-xylo-hexofuranosyl-(1→3)-d-Manp
  作者：Carla Marino、Alejandro Chiocconi、Oscar Varela、Rosa M de Lederkremer

  DOI：10.1016/s0008-6215(98)00214-6

  日期：1998.10

  A convenient synthesis of free beta-D-Galf-(1 --> 3)-D-Manp (8a) is reported. The disaccharide is present as external unit in the lipopeptidophosphoglycan (LPPG) of Trypanosoma cruzi and internally in the lipophosphoglycan (LPG) of Leishmania. Condensation of 2,5,6-tri-O-benzoyl-D-mannono-1,4-lactone (1) with 1,2,3,5,6-penta-O-benzoyl-D-galactofuranose promoted by SnCl4, led to the B-glycosyl-lactone, a key intermediate for disaccharide 8a, readily obtained by successive reduction of the lactone with diisoamylborane and debenzoylation. As in the LPG of Leishmania the HO-3 group of the galactofuranose is glycosylated by alpha-D-Galp, we also synthesized 3-deoxy-beta D-xylo-hexofuranosyl-(1 --> 3)-D-Manp (8b) and p-nitrophenyl 3-deoxy-beta-D-xylo-hexofuranoside for studying the influence of HO-3 in the interaction with specific glycosidases. The disaccharide 8a, and its corresponding alditol, were good substrates for the beta-D-galactofuranosidase from Penicillium fellutanum, whereas the 3-deoxyglycosides were not hydrolyzed by the enzyme. (C) 1998 Elsevier Science Ltd. All rights reserved.