O-methyl-(N-benzenecarboxamido)-L-serinyl 2,3,4,6-tetra-O-methyl-D-glucopyranoside | 1416849-95-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: O-methyl-(N-benzenecarboxamido)-L-serinyl 2,3,4,6-tetra-O-methyl-D-glucopyranoside
• 英文别名: methyl (2S)-2-benzamido-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 1416849-95-0
• 化学式: C₂₁H₃₁NO₉
• 分子量: 441.478
• InChiKey: OKTIMYDGBMRZFU-FZQNIYIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-benzoyl-L-serine methyl ester 、 p-methoxyphenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 在 三氯溴甲烷 、 六氟异丙醇 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以0.037 g的产率得到O-methyl-(N-benzenecarboxamido)-L-serinyl 2,3,4,6-tetra-O-methyl-D-glucopyranoside
  参考文献：
  名称：

  Visible Light Mediated Activation and O-Glycosylation of Thioglycosides

  摘要：

  Visible light catalysis allows the efficient construction of single electron transfer (SET) redox cycles that result in minimal formation of byproducts and proceed under exogenous control of a removable light source. The O-glycosylation of thioglycosides via visible light photoredox chemistry is reported. Mechanistic studies show that the reaction is fully light responsive and support a mechanism involving decomposition of an oxidatively generated sulfur radical cation and propagation via reduction of the thiol side product.

  DOI：

  10.1021/ol302941q

文献信息

• Visible Light Mediated Activation and <i>O-</i>Glycosylation of Thioglycosides
  作者：Walter J. Wever、Maris A. Cinelli、Albert A. Bowers

  DOI：10.1021/ol302941q

  日期：2013.1.4

  Visible light catalysis allows the efficient construction of single electron transfer (SET) redox cycles that result in minimal formation of byproducts and proceed under exogenous control of a removable light source. The O-glycosylation of thioglycosides via visible light photoredox chemistry is reported. Mechanistic studies show that the reaction is fully light responsive and support a mechanism involving decomposition of an oxidatively generated sulfur radical cation and propagation via reduction of the thiol side product.