benzyl 2-O-benzoyl-3-O-benzyl-6-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside | 316156-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-O-benzoyl-3-O-benzyl-6-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside
• 英文别名: 1-O-[[(2R,3R,4S,5S,6S)-5-benzoyloxy-3-hydroxy-4,6-bis(phenylmethoxy)oxan-2-yl]methyl] 3-O-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl] propanedioate
• CAS: 316156-98-6
• 化学式: C₅₉H₆₂O₁₄S
• 分子量: 1027.2
• InChiKey: YODGREQZVLZAFP-IIASPNFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  74
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzoyl-3-O-benzyl-6-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.08h， 生成 benzyl O-(6-O-benzoyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2,6-di-O-benzoyl-3-O-benzyl α-D-mannopyranoside
  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 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 benzyl 2-O-benzoyl-3-O-benzyl-6-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside
  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

• ——
  作者：Gregor Lemanski、Thomas Ziegler

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

  日期：2000.10.4

  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.