phenylsulfenyl 2,2',3,3',4',6,6'-hepta-O-benzyl-β-D-lactopyranoside | 1072785-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylsulfenyl 2,2',3,3',4',6,6'-hepta-O-benzyl-β-D-lactopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6S)-6-(benzenesulfinyl)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1072785-97-7
• 化学式: C₆₇H₆₈O₁₁S
• 分子量: 1081.34
• InChiKey: BFTMNZHPTOUURQ-CNKZKWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  79
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  phenylsulfenyl 2,2',3,3',4',6,6'-hepta-O-benzyl-β-D-lactopyranoside 、 烯丙基三甲基硅烷 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(2R,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyl-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到phenylsulfenyl 2,2',3,3',4',6,6'-hepta-O-benzyl-β-D-lactopyranoside
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s

文献信息

• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.