4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N-benzyloxycarbonyl-D-tyrosine benzyl ester | 920306-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N-benzyloxycarbonyl-D-tyrosine benzyl ester
• CAS: 920306-98-5
• 化学式: C₅₈H₅₇NO₁₀
• 分子量: 928.091
• InChiKey: QSVIABUPBRQUKC-CGFNEYCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.34
• 重原子数：
  69.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  120.01
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N-benzyloxycarbonyl-D-tyrosine benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 以75%的产率得到4-O-(β-D-glucopyranosyl)-D-tyrosine
  参考文献：
  名称：

  Synthesis and biological activities of analogs of d-glucosyl-l-tyrosine, a humoral factor that stimulates transcription of the acyl-CoA binding protein in the pheromone gland of the Silkmoth, Bombyx mori

  摘要：

  beta-D-Glucosyl-O-L-tyrosine (1) is a Immoral factor that stimulates transcription of the acyl-CoA binding protein (ACBP) in the pheromone gland of the Silkmoth, Bombyx mori. This paper describes stereoselective synthesis of five analogs that changed the sugar and/or amino acid part in 1 and their stimulatory activities on the ACBP transcription in the pheromone gland of B. mori. Among the analogs tested, beta-D-galactosyl-O-L-tyrosine showed a 115 potency compared to the activity of 1. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.008
• 作为产物：
  描述：

  N-苄氧羰基-D-酪氨酸 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N-benzyloxycarbonyl-D-tyrosine benzyl ester
  参考文献：
  名称：

  Synthesis and biological activities of analogs of d-glucosyl-l-tyrosine, a humoral factor that stimulates transcription of the acyl-CoA binding protein in the pheromone gland of the Silkmoth, Bombyx mori

  摘要：

  beta-D-Glucosyl-O-L-tyrosine (1) is a Immoral factor that stimulates transcription of the acyl-CoA binding protein (ACBP) in the pheromone gland of the Silkmoth, Bombyx mori. This paper describes stereoselective synthesis of five analogs that changed the sugar and/or amino acid part in 1 and their stimulatory activities on the ACBP transcription in the pheromone gland of B. mori. Among the analogs tested, beta-D-galactosyl-O-L-tyrosine showed a 115 potency compared to the activity of 1. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.008