benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,3-di-O-benzoyl-α-D-glucopyranoside 6,6'-malonate | 316188-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,3-di-O-benzoyl-α-D-glucopyranoside 6,6'-malonate
• CAS: 316188-38-2
• 化学式: C₅₇H₅₄O₁₅
• 分子量: 979.047
• InChiKey: JSIYJBSOIWEVQT-LVCNTYGASA-N

反应信息

• 作为反应物：
  描述：

  benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,3-di-O-benzoyl-α-D-glucopyranoside 6,6'-malonate 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 benzyl O-(6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u
• 作为产物：
  描述：

  benzyl 2,3-di-O-benzoyl-6-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,3-di-O-benzoyl-α-D-glucopyranoside 6,6'-malonate
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u