2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole | 957476-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole
• 英文别名: [(2R,3R,4S,5R,6R)-6-(1,3-benzoxazol-2-ylsulfanyl)-3,4-dibenzoyloxy-5-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 957476-29-8
• 化学式: C₄₁H₃₃NO₉S
• 分子量: 715.78
• InChiKey: RVSVPXCYEHXKEM-OXGMQFBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole 、 双丙酮半乳糖 在 5A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 14.0h， 以13%的产率得到6-O-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-α-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Revisiting the Armed−Disarmed Concept:  The Importance of Anomeric Configuration in the Activation of S-Benzoxazolyl Glycosides

  摘要：

  The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.

  DOI：

  10.1021/ol701466u
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-2-O-benzyl-α-D-glucopyranosyl bromide 在 三苯基膦 、 silver carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole
  参考文献：
  名称：

  Revisiting the Armed−Disarmed Concept:  The Importance of Anomeric Configuration in the Activation of S-Benzoxazolyl Glycosides

  摘要：

  The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.

  DOI：

  10.1021/ol701466u

文献信息

• Revisiting the Armed−Disarmed Concept:  The Importance of Anomeric Configuration in the Activation of <i>S</i>-Benzoxazolyl Glycosides
  作者：David Crich、Ming Li

  DOI：10.1021/ol701466u

  日期：2007.10.1

  The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.