methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate | 908608-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate
• CAS: 908608-60-6
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: VBJNSDCPJLVQQQ-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate 在 D(+)-10-樟脑磺酸 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.92h， 生成 5-[(2S,3S,4R)-4-aminomethyl-3-hydroxyoxetan-2-yl]-3-p-methoxyphenyl-1,2,4-oxadiazole trifluoroacetate
  参考文献：
  名称：

  Libraries on Oxetane δ-Amino Acid Scaffolds: Syntheses and Evaluation of Physicochemical and Metabolic Properties

  摘要：

  Oxetane delta-amino acids were investigated as scaffolds to generate oxetane-based libraries. As pharmacophores, oxadiazoles and triazoles were built up on the scaffolds. Important physicochemical properties of target compounds were predicted in silico, and some physicochemical (solubility, logD, pKa values, permeation through artificial membranes) and metabolic (intrinsic clearance) properties were determined experimentally. The compounds synthesized exhibited the desired ADMETox properties. From an in silico point of view, this work adds valuable information for the refinement of prediction tools.

  DOI：

  10.1080/07328303.2011.609627
• 作为产物：
  描述：

  3,5-di-O-benzyl-D-xylofuranose 在 palladium on activated charcoal 吡啶 、 叠氮化锂 、 4 A molecular sieve 、 氢气 、 溴 、 potassium carbonate 、 barium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 9.17h， 生成 methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate
  参考文献：
  名称：

  Oxetane δ‐Amino Acids: Chemoenzymatic Synthesis of 2,4‐Anhydro‐5‐N‐(t‐butoxycarbonyl)amino‐D‐lyxonic Acid

  摘要：

  Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate ( 4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate (9). While transesterification of 4 under basic reaction conditions was straightforward, an analogous reaction with 9 was not successful. After screening of several lipases, the enzymatic transesterification of 9 was achieved with lipase L2 from Candida antarctica to furnish the title compound 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid in excellent yield. The stereochemistry at the oxetane ring was proven by an x-ray structure of the intermediate methyl 2,4-anhydro-5-azido-D-lyxonate.[GRAPHICS]

  DOI：

  10.1080/07328300600732485