2,5-diamino-2,5-dideoxy-D-glucono-1,5-lactam-6-phosphate | 1432490-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2,5-diamino-2,5-dideoxy-D-glucono-1,5-lactam-6-phosphate
• 英文别名: [(2R,3R,4R,5R)-5-amino-3,4-dihydroxy-6-oxopiperidin-2-yl]methyl dihydrogen phosphate
• CAS: 1432490-78-2
• 化学式: C₆H₁₃N₂O₇P
• 分子量: 256.152
• InChiKey: PJJGCHGDZNTGDW-TXICZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  162
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-amino-2-(benzyloxycarbonyl)amino-2,5-dideoxy-3,4-bis-O-(4-(pivaloylamino)benzyl)-D-glucono-1,5-lactam 在 吡啶 、 三氯氧磷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 10 wt% Pd(OH)2 on carbon 、 碳酸氢铵 作用下， 以 水 、 氯仿 、 甲醇 为溶剂， 反应 0.75h， 以99%的产率得到2,5-diamino-2,5-dideoxy-D-glucono-1,5-lactam-6-phosphate
  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