benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1 -> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate | 220009-64-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1 -> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate
• 英文别名: benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate
• CAS: 220009-64-3
• 化学式: C₅₇H₅₆O₁₄
• 分子量: 965.063
• InChiKey: QOHBQWHAIRVAIF-UQNRIQJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  71.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1 -> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 Benzoic acid (2S,3S,4S,5S,6R)-2-benzyloxy-6-benzyloxymethyl-4-hydroxy-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 4, 9, 14, 16, 22, 28, 33, 41, and 46, having a benzyl-protected 1-thiomannosyl donor linked through its position 6 via malonate and succinate tethers to various positions of glucosamine, galactose, mannose, and rhamnose accepters, were prepared and cyclized to the corresponding disaccharides. The configuration at the anomeric center of the products strongly depended on the position of the tt ther in the acceptor part and could be predicted from the calculated thermodynamic stability of the products. No strong dependence of the diastereoselectivity of the intramolecular glycosylations on the activation conditions and the solvent was observed.

  DOI：

  10.1002/1522-2675(20001004)83:10<2676::aid-hlca2676>3.0.co;2-k
• 作为产物：
  描述：

  benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 3 A molecular sieve 、 4 Angstroem MS 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 30.0h， 生成 benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1 -> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 4, 9, 14, 16, 22, 28, 33, 41, and 46, having a benzyl-protected 1-thiomannosyl donor linked through its position 6 via malonate and succinate tethers to various positions of glucosamine, galactose, mannose, and rhamnose accepters, were prepared and cyclized to the corresponding disaccharides. The configuration at the anomeric center of the products strongly depended on the position of the tt ther in the acceptor part and could be predicted from the calculated thermodynamic stability of the products. No strong dependence of the diastereoselectivity of the intramolecular glycosylations on the activation conditions and the solvent was observed.

  DOI：

  10.1002/1522-2675(20001004)83:10<2676::aid-hlca2676>3.0.co;2-k

文献信息

• Synthesis ofβ-Mannosides via Prearranged Glycosides
  作者：Thomas Ziegler、Gregor Lemanski

  DOI：10.1002/(sici)1521-3773(19981204)37:22<3129::aid-anie3129>3.0.co;2-8

  日期：1998.12.4

  The choice of activator is decisive for whether the α-(1→4)-linked disaccharide 2 α or the anomeric compound 2 β is formed from the prearranged glycoside 1. Other β-mannosylsaccharides can also be synthesized selectively by intramolecular glycosylation. Bn=benzyl, Bz=benzoyl, MeOTf= methyl trifluoromethanesulfonate, NIS=N-iodosuccinimide.