ethyl 2-((2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate | 1259515-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-((2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
• 英文别名: ethyl 2-[(2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]acetate
• CAS: 1259515-55-3
• 化学式: C₃₈H₄₁N₃O₇
• 分子量: 651.759
• InChiKey: XRRZKZIRDIUPQS-KFHNNOKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  ((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 在 叠氮基三甲基硅烷 、 碘 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到ethyl 2-((2S,3R,4S,5R,6R)-2-azido-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Molecular iodine-promoted N- and C-glycosylation of 1-C-alkyl (or phenyl)-glycopyranoses

  摘要：

  Molecular iodine efficiently promoted the N- and C-glycosylation of hemiketals with Me3SiN3 and Me3SiCN, respectively. Using this method we have prepared diverse functional N- and C-ketosides, which could serve as useful synthons for the preparation of unnatural glycosyl amino acids or glycopeptides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.124

文献信息

• Molecular iodine-promoted N- and C-glycosylation of 1-C-alkyl (or phenyl)-glycopyranoses
  作者：A.P. John Pal、Asadulla Mallick、Y. Suman Reddy、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2010.09.124

  日期：2010.12

  Molecular iodine efficiently promoted the N- and C-glycosylation of hemiketals with Me3SiN3 and Me3SiCN, respectively. Using this method we have prepared diverse functional N- and C-ketosides, which could serve as useful synthons for the preparation of unnatural glycosyl amino acids or glycopeptides. (C) 2010 Elsevier Ltd. All rights reserved.