3-O-allyl-1,2-di-O-p-methoxybenzyl-sn-glycerol | 190779-63-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-allyl-1,2-di-O-p-methoxybenzyl-sn-glycerol
• CAS: 190779-63-6
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: ZTEDJDJAZFSCKD-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  27.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-O-allyl-1,2-di-O-p-methoxybenzyl-sn-glycerol 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到(2S)-2,3-di-p-methoxybenzyl glycerol
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8
• 作为产物：
  描述：

  (S)-4-((allyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 17.25h， 生成 3-O-allyl-1,2-di-O-p-methoxybenzyl-sn-glycerol
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8