phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxan-2-yl]methyl pyridine-2-carboxylate
• 化学式: C₃₉H₃₇NO₆S
• 分子量: 647.792
• InChiKey: DQYMSIAJAICJTI-FVGDZVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside 在 palladium(II) bromide 、 DMTST 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 以59.184%的产率得到
  参考文献：
  名称：

  6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity

  摘要：

  Remote 6-O-picolinyl or 6-O-picoloyl substituents often provide high beta-selectivity due to H-bond-mediated aglycone delivery (HAD). Herein it has been demonstrated that if the nitrogen atom of the 6-O-picolinyl or picoloyl moiety is temporarily blocked by coordination to a metal center (Pd), it cannot engage in HAD-mediated beta-glycosylation. Hence, the stereoselectivity of 6-O-picolinyl/picoloyl-assisted glycosylations can be "switched" to alpha-selectivity.

  DOI：

  10.1021/acs.orglett.5b02110
• 作为产物：
  描述：

  2-吡啶甲酸 、 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到phenyl 2,3,4-tri-O-benzyl-6-O-picoloyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity

  摘要：

  Remote 6-O-picolinyl or 6-O-picoloyl substituents often provide high beta-selectivity due to H-bond-mediated aglycone delivery (HAD). Herein it has been demonstrated that if the nitrogen atom of the 6-O-picolinyl or picoloyl moiety is temporarily blocked by coordination to a metal center (Pd), it cannot engage in HAD-mediated beta-glycosylation. Hence, the stereoselectivity of 6-O-picolinyl/picoloyl-assisted glycosylations can be "switched" to alpha-selectivity.

  DOI：

  10.1021/acs.orglett.5b02110