ethyl 4-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside | 1415590-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside
• CAS: 1415590-65-6
• 化学式: C₁₄H₃₀O₄SSi
• 分子量: 322.541
• InChiKey: UTADJSTZLMMSPH-IEECTRCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.75h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,4-di-O-benzyl-3-O-picoloyl-β-L-rhamnopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Effect of Remote Picolinyl and Picoloyl Substituents on the Stereoselectivity of Chemical Glycosylation

  摘要：

  O-Picolinyl and O-picoloyl groups at remote positions (C-3, C-4, and C-6) can mediate glycosylation reactions by providing high or even complete facial selectivity for the attack of the glycosyl acceptor. The set of data presented herein offers a strong evidence of the intermolecular H-bond tethering between the glycosyl donor and glycosyl acceptor counterparts while providing a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging glycosidic linkages including alpha-gluco, beta-manno, and beta-rhamno have seen obtained with high or complete stereocontrol.

  DOI：

  10.1021/ja307355n
• 作为产物：
  描述：

  ethyl 4-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以83%的产率得到ethyl 4-O-tert-butyldimethylsilyl-1-thio-β-L-rhamnopyranoside
  参考文献：
  名称：

  Effect of Remote Picolinyl and Picoloyl Substituents on the Stereoselectivity of Chemical Glycosylation

  摘要：

  O-Picolinyl and O-picoloyl groups at remote positions (C-3, C-4, and C-6) can mediate glycosylation reactions by providing high or even complete facial selectivity for the attack of the glycosyl acceptor. The set of data presented herein offers a strong evidence of the intermolecular H-bond tethering between the glycosyl donor and glycosyl acceptor counterparts while providing a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging glycosidic linkages including alpha-gluco, beta-manno, and beta-rhamno have seen obtained with high or complete stereocontrol.

  DOI：

  10.1021/ja307355n