diethyl (2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)phosphonate | 1401709-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl (2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranosyl)phosphonate
• 英文别名: (2S,3R,4R,5S,6R)-2-[diethoxy(oxido)phosphaniumyl]-5-fluoro-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1401709-37-2
• 化学式: C₃₁H₃₈FO₇P
• 分子量: 572.611
• InChiKey: GNGIFZFNZAZCLQ-NBCLCUQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-O-acetyl-2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-D-galactopyranose 、 亚磷酸三乙酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以53%的产率得到diethyl (2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranosyl)phosphonate
  参考文献：
  名称：

  Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal

  摘要：

  Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-alpha-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl-D-galactal and allyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.07.015