benzoxazol-2-yl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-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: benzoxazol-2-yl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[[(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]sulfanyl-1,3-benzoxazole
• 化学式: C₆₈H₆₇NO₁₁S
• 分子量: 1106.35
• InChiKey: FDJWNMMSUHFQAP-YBMROTNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  81
• 可旋转键数：
  27
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

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 、 benzoxazol-2-yl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以92%的产率得到methyl O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1→6)-O-(2,3,4-tri-O-benzyl-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected Orthogonality of S-Benzoxazolyl and S-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly

  摘要：

  Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the "thioimidate-only orthogonal strategy". Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leaving groups was achieved by fine-tuning of the activation conditions. Preferential glycosidation of a certain thioimidate is not simply determined by the strength of activating reagents; instead, the type of activation-direct vs indirect-comes to the fore and plays the key role.

  DOI：

  10.1021/ol802740b

文献信息

• Unexpected Orthogonality of <i>S</i>-Benzoxazolyl and <i>S</i>-Thiazolinyl Glycosides: Application to Expeditious Oligosaccharide Assembly
  作者：Sophon Kaeothip、Papapida Pornsuriyasak、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1021/ol802740b

  日期：2009.2.19

  Thorough mechanistic studies of the alkylation pathway for the activation of glycosyl thioimidates have led to the development of the "thioimidate-only orthogonal strategy". Discrimination among S-thiazolinyl (STaz) and S-benzoxazolyl (SBox) anomeric leaving groups was achieved by fine-tuning of the activation conditions. Preferential glycosidation of a certain thioimidate is not simply determined by the strength of activating reagents; instead, the type of activation-direct vs indirect-comes to the fore and plays the key role.