(S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 649745-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 649745-80-2
• 化学式: C₁₇H₂₉NO₅
• 分子量: 327.421
• InChiKey: RWABYYNUTTVMLV-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 钯 氢气 、 臭氧 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， -78.0 ℃ 、310.26 kPa 条件下， 反应 13.0h， 生成 (2S,3S,4R)-2-羟甲基四氢吡咯-3,4-二醇
  参考文献：
  名称：

  Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-l-iminoribitol

  摘要：

  The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.050
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 indium 、 Amberlyst(R) 15H 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-l-iminoribitol

  摘要：

  The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.050

文献信息

• Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-l-iminoribitol
  作者：Marco Lombardo、Sebastiano Licciulli、Claudio Trombini

  DOI：10.1016/j.tetlet.2003.10.050

  日期：2003.12

  The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor. (C) 2003 Elsevier Ltd. All rights reserved.