2-amino-6-azido-2,6-dideoxy-D-glucose trifluoroacetate salt | 1432490-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-6-azido-2,6-dideoxy-D-glucose trifluoroacetate salt
• CAS: 1432490-87-3
• 化学式: C₂HF₃O₂*C₆H₁₂N₄O₄
• 分子量: 318.21
• InChiKey: JIKPPJCGQPAPSG-OCOFDJSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  182.0
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  triethylsilyl 6-azido-2,6-dideoxy-2-((phenylmethoxy)carbonyl)amino-3,4-bis-O-(triethylsilyl)-α-D-glucopyranoside 、 三氟乙酸 以 水 为溶剂， 反应 3.0h， 以42.857%的产率得到
  参考文献：
  名称：

  Glucosamine and Glucosamine-6-phosphate Derivatives: Catalytic Cofactor Analogues for the glmS Ribozyme

  摘要：

  Two analogues of glucosamine-6-phosphate (GlcN6P, 1) and five of glucosamine (GlcN, 2) were prepared for evaluation as catalytic cofactors of the glmS ribozyme, a bacterial gene-regulatory RNA that controls cell wall biosynthesis. Glucosamine and allosamine with 3-azido substitutions were prepared by S(N)2 reactions of the respective 1,2,4,6-protected sugars; final acidic hydrolysis afforded the fully deprotected compounds as their TFA salts. A 6-phospho-2-aminoglucolactam (31) was prepared from glucosamine in a 13-step synthesis, which included a late-stage POCl3-phosphorylation. A simple and widely applicable 2-step procedure with the triethylsilyl (TES) protecting group was developed to selectively expose the 6-OH group in N-protected glucosamine analogues, which provided another route to chemical phosphorylation. Mitsunobu chemistry afforded 6-cyano (35) and 6-azido (36) analogues of GlcN-(Cbz), and the selectivity for the 6-position was confirmed by NMR (COSY, HMBC, HMQC) experiments. Compound 36 was converted to the fully deprotected 6-azido-GlcN (37) and 2,6-diaminoglucose (38) analogues. A 2-hydroxylamino glucose (42) analogue was prepared via an oxaziridine (41). Enzymatic phosphorylation of 42 and chemical phosphorylation of its 6-OH precursor (43) were possible, but 42 and the 6-phospho product (44) were unstable under neutral or basic conditions. Chemical phosphorylation of the previously described 2-guanidinyl-glucose (46) afforded its 6-phospho analogue (49) after final deprotection.

  DOI：

  10.1021/jo400192e