(3aS,3'R,4R,6R,6aR)-2'-tert-butyl 3'-ethyl 6-methoxy-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-2',3'-dicarboxylate | 1268670-37-6

• 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: (3aS,3'R,4R,6R,6aR)-2'-tert-butyl 3'-ethyl 6-methoxy-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-2',3'-dicarboxylate
• CAS: 1268670-37-6
• 化学式: C₁₉H₃₁NO₉
• 分子量: 417.456
• InChiKey: ZUGBAGCQYNTRJK-LNAJDVRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  101.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3aS,3'R,4R,6R,6aR)-2'-tert-butyl 3'-ethyl 6-methoxy-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-2',3'-dicarboxylate 在 氢气 、 硼酸 、 magnesium sulfate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以50%的产率得到(2R)-ethyl 2-(tert-butoxycarbonylamino)-4-((3aS,6aS)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)butanoate
  参考文献：
  名称：

  Synthesis of C-glycosylated amino acids by hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals

  摘要：

  C-Glycoamino acids bearing a variety of sugar moieties were prepared by the hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to exo-glycals. The reaction proceeds smoothly to yield spirocyclic oxazines that can be converted into useful products by several hydrogenolytic techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.12.001
• 作为产物：
  描述：

  ethyl (2R,3R,4S,5R)-3,4-isopropylidenedioxy-2-methoxy-1,6-dioxa-7-azaspiro[4.5]dec-7-ene-8-carboxylate 在 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (3aS,3'R,4R,6R,6aR)-2'-tert-butyl 3'-ethyl 6-methoxy-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-2',3'-dicarboxylate
  参考文献：
  名称：

  Synthesis of C-glycosylated amino acids by hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to exo-glycals

  摘要：

  C-Glycoamino acids bearing a variety of sugar moieties were prepared by the hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to exo-glycals. The reaction proceeds smoothly to yield spirocyclic oxazines that can be converted into useful products by several hydrogenolytic techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.12.001