1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene | 444150-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene
• 英文别名: (2S,3S,4R,5R,6R)-2-[[4-(bromomethyl)-2-phenylmethoxyphenyl]methyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 444150-27-0
• 化学式: C₄₉H₄₉BrO₆
• 分子量: 813.828
• InChiKey: YKNHLYANVPWIFE-DBTIBLCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  56
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.33h， 生成 (2S)-2-amino-3-[3-phenylmethoxy-4-[[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]phenyl]propanoic acid
  参考文献：
  名称：

  A Novel General Route for the Synthesis of C-Glycosyl Tyrosine Analogues

  摘要：

  A general method for the synthesis of C-glycosyl amino acids is described here. The stereoisomerically pure tyrosine analigues alpha-L-4 and beta-L-6 are prepared in reasonable overall yields from all l derivatives 10 and 11. The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.

  DOI：

  10.1002/1521-3765(20020415)8:8<1872::aid-chem1872>3.0.co;2-a
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-ethanal 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 氯甲酸乙酯 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 23.5h， 生成 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene
  参考文献：
  名称：

  A Novel General Route for the Synthesis of C-Glycosyl Tyrosine Analogues

  摘要：

  A general method for the synthesis of C-glycosyl amino acids is described here. The stereoisomerically pure tyrosine analigues alpha-L-4 and beta-L-6 are prepared in reasonable overall yields from all l derivatives 10 and 11. The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.

  DOI：

  10.1002/1521-3765(20020415)8:8<1872::aid-chem1872>3.0.co;2-a

文献信息

• A Novel General Route for the Synthesis of C-Glycosyl Tyrosine Analogues
  作者：Elisabetta Brenna、Claudio Fuganti、Piero Grasselli、Stefano Serra、Sabrina Zambotti

  DOI：10.1002/1521-3765(20020415)8:8<1872::aid-chem1872>3.0.co;2-a

  日期：2002.4.15

  A general method for the synthesis of C-glycosyl amino acids is described here. The stereoisomerically pure tyrosine analigues alpha-L-4 and beta-L-6 are prepared in reasonable overall yields from all l derivatives 10 and 11. The key step is a benzannulation procedure which is employed in the creation of the aromatic ring that bears the amino acid function.