benzyl 4,6-di-O-benzylidene-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside | 262605-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4,6-di-O-benzylidene-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside
• CAS: 262605-47-0
• 化学式: C₆₀H₅₉NO₁₄S
• 分子量: 1050.19
• InChiKey: YRWNRKWBSQFNBV-JCMMVRDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.79
• 重原子数：
  76.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  163.82
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl 4,6-di-O-benzylidene-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside 在 三乙基硅烷 、 4 A molecular sieve 、 三氟乙酸 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 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
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside 、 benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-glucopyranoside 在 三正丁胺 、 2-氯-1-甲基吡啶碘化物 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以80%的产率得到benzyl 4,6-di-O-benzylidene-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside
  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