5,6-dideoxy-5-(hexadecylamino)-1,2-O-isopropylidene-3-O-methyl-heptofuranuronic acid

• 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: 5,6-dideoxy-5-(hexadecylamino)-1,2-O-isopropylidene-3-O-methyl-heptofuranuronic acid
• 英文别名: 3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(hexadecylamino)propanoic acid
• 化学式: C₂₇H₅₁NO₆
• 分子量: 485.705
• InChiKey: WBTNUDCAORKYJQ-UGLONUFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-Hexadecylamino-3-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propionic acid ethyl ester 在 水 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 50.0h， 以75%的产率得到5,6-dideoxy-5-(hexadecylamino)-1,2-O-isopropylidene-3-O-methyl-heptofuranuronic acid
  参考文献：
  名称：

  Synthesis of glycosylated β-amino acids as new class of antitubercular agents

  摘要：

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01398-3