tert-butyl (2S,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutanoate | 849829-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutanoate
• CAS: 849829-40-9
• 化学式: C₂₃H₃₇NO₉
• 分子量: 471.548
• InChiKey: AAMJYSZZYKYZLO-MZRXWKAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  151.62
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutanoate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N^α-(4,4-dimethyl-2,6-dioxocyclohexylidenemethylene)-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-L-threonine
  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 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,3R)-2-[(4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino]-3-[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutanoate
  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