tert-butyl (2S)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxypropanoate | 849829-42-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl (2S)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxypropanoate
• CAS: 849829-42-1
• 化学式: C₂₈H₄₁NO₁₂
• 分子量: 583.633
• InChiKey: SZGGAZMGTLRJFD-AXZJAMBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxypropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到N^α-(4,4-dimethyl-2,6-dioxocyclohexylidenemethylene)-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-L-serine
  参考文献：
  名称：

  Nα-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation

  摘要：

  N-alpha-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, L-threonine and L-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient alpha-O-glycosylation with an L-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.055
• 作为产物：
  描述：

  2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 在 palladium on activated charcoal 吡啶 、 四乙基溴化铵 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 tert-butyl (2S)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxypropanoate
  参考文献：
  名称：

  Nα-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation

  摘要：

  N-alpha-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, L-threonine and L-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient alpha-O-glycosylation with an L-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.055