[(2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-bromoethoxy)-4-hydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate | 139639-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-bromoethoxy)-4-hydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
• CAS: 139639-78-4
• 化学式: C₃₅H₃₇BrO₁₄
• 分子量: 761.574
• InChiKey: PRGFMOSKODGDOF-JCDRPJJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  197
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate 、 [(2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-bromoethoxy)-4-hydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate 在 甲基硫基溴化物 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到
  参考文献：
  名称：

  Exceptionally high yield in glycosylation with sialic acid. Synthesis of a GM3 glycoside.

  摘要：

  Exceptionally high yield was obtained in the glycosylation of HO-3 of lactose derivative 1 with xanthate 2 as sialosyl donor using methylsulfenyl triflate in acetonitrile/dichloromethane at -60-degrees-C. The yield of the sialosyl oligosaccharide was dependent on the amount of sialosyl donor used. The yields were 63, 75 and 82% using 1.1, 1.68 and 2.0 equivalents respectively of donor and 1.0 equivalent of acceptor.

  DOI：

  10.1016/s0040-4039(00)77688-x
• 作为产物：
  描述：

  苯甲酰氯 、 2-bromoethyl 4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 生成 [(2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6R)-5-benzoyloxy-2-(benzoyloxymethyl)-6-(2-bromoethoxy)-4-hydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Exceptionally high yield in glycosylation with sialic acid. Synthesis of a GM3 glycoside.

  摘要：

  Exceptionally high yield was obtained in the glycosylation of HO-3 of lactose derivative 1 with xanthate 2 as sialosyl donor using methylsulfenyl triflate in acetonitrile/dichloromethane at -60-degrees-C. The yield of the sialosyl oligosaccharide was dependent on the amount of sialosyl donor used. The yields were 63, 75 and 82% using 1.1, 1.68 and 2.0 equivalents respectively of donor and 1.0 equivalent of acceptor.

  DOI：

  10.1016/s0040-4039(00)77688-x

文献信息

• PEPTIDE-CARBOHYDRATE CONJUGATES GENERATING T-CELL IMMUNITY
  申请人：AstraZeneca AB

  公开号：EP0675733B1

  公开（公告）日：2000-12-06
• US5807559A
  申请人：——

  公开号：US5807559A

  公开（公告）日：1998-09-15
• US6033669A
  申请人：——

  公开号：US6033669A

  公开（公告）日：2000-03-07
• Exceptionally high yield in glycosylation with sialic acid. Synthesis of a GM3 glycoside.
  作者：Hans Lönn、Kristina Stenvall

  DOI：10.1016/s0040-4039(00)77688-x

  日期：1992.1

  Exceptionally high yield was obtained in the glycosylation of HO-3 of lactose derivative 1 with xanthate 2 as sialosyl donor using methylsulfenyl triflate in acetonitrile/dichloromethane at -60-degrees-C. The yield of the sialosyl oligosaccharide was dependent on the amount of sialosyl donor used. The yields were 63, 75 and 82% using 1.1, 1.68 and 2.0 equivalents respectively of donor and 1.0 equivalent of acceptor.