N,N-diethyl-2,3-anhydro-4-deoxy-6,8-O-benzylidene-D-glycero-D-ido and D-galacto-octonamide | 219736-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: N,N-diethyl-2,3-anhydro-4-deoxy-6,8-O-benzylidene-D-glycero-D-ido and D-galacto-octonamide
• CAS: 219736-61-5
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: YUPCBUBNRJYVKL-YFQVSBBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  91.76
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N,N-diethyl-2,3-anhydro-4-deoxy-6,8-O-benzylidene-D-glycero-D-ido and D-galacto-octonamide 在 吡啶 作用下， 反应 12.0h， 以54%的产率得到N,N-diethyl-2,3-anhydro-4-deoxy-5,7-di-O-acetyl-6,8-O-benzylidene-D-glycero-D-ido and D-galacto-octonamide
  参考文献：
  名称：

  Reaction of O-Benzyl- and 4,6-O-Benzylidene-d-Gluco- and d-Galactopyranose Derivatives with Amide-Stabilized Sulfur Ylides:  Stereoselectivity and Reactivity

  摘要：

  The reaction of N,N-diethyl-2-(dimethylsulfuranylidene)acetamide (1) with protected monosaccharides has been extended to several O-benzyl- and 4,6-O-Benzylidene-D-gluco- and -D-galactopyranose derivatives. When the monosaccharide is 2,3,4,6-tetra-O-benzyl-D-glucose (6) or D-galactose (9), elimination of the 3-benzyloxy substituent occurs, to give the unsaturated epoxyamides 7 and 10, respectively, in reasonable yields and poor stereoselectivity. On the other hand, the, reaction of 1 with the 4,6-O-benzylidene-D-glucopyranose derivatives 11, 14, and 17 yielded the corresponding epoxyamides 12, 15a:15b, and 18a:18b in good yields and variable stereoselectivity. In accordance with previous studies concerning the configurational assignments for the epoxide derivatives 3, 5a, and 21,(6) obtained from 2, 4, and 20, respectively, the present article confirms the role of the hydroxyl group at C-2 on the stereselectivity of the reaction. Thus, when the C-2 OH is unprotected (4, 11, 20), the major epoxide formed has the configuration 2S, 3R (epoxyamides 5a, 12, and 21). Conversely, derivatives with the hydroxyl group protected at C-2, or a-deoxy sugars (2, 14, and 17), yield as the major epoxides the corresponding 2R, 3S isomers (3, 15b, and 18b).

  DOI：

  10.1021/jo971824a
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 N,N-diethyl-2,3-anhydro-4-deoxy-6,8-O-benzylidene-D-glycero-D-ido and D-galacto-octonamide
  参考文献：
  名称：

  Reaction of O-Benzyl- and 4,6-O-Benzylidene-d-Gluco- and d-Galactopyranose Derivatives with Amide-Stabilized Sulfur Ylides:  Stereoselectivity and Reactivity

  摘要：

  The reaction of N,N-diethyl-2-(dimethylsulfuranylidene)acetamide (1) with protected monosaccharides has been extended to several O-benzyl- and 4,6-O-Benzylidene-D-gluco- and -D-galactopyranose derivatives. When the monosaccharide is 2,3,4,6-tetra-O-benzyl-D-glucose (6) or D-galactose (9), elimination of the 3-benzyloxy substituent occurs, to give the unsaturated epoxyamides 7 and 10, respectively, in reasonable yields and poor stereoselectivity. On the other hand, the, reaction of 1 with the 4,6-O-benzylidene-D-glucopyranose derivatives 11, 14, and 17 yielded the corresponding epoxyamides 12, 15a:15b, and 18a:18b in good yields and variable stereoselectivity. In accordance with previous studies concerning the configurational assignments for the epoxide derivatives 3, 5a, and 21,(6) obtained from 2, 4, and 20, respectively, the present article confirms the role of the hydroxyl group at C-2 on the stereselectivity of the reaction. Thus, when the C-2 OH is unprotected (4, 11, 20), the major epoxide formed has the configuration 2S, 3R (epoxyamides 5a, 12, and 21). Conversely, derivatives with the hydroxyl group protected at C-2, or a-deoxy sugars (2, 14, and 17), yield as the major epoxides the corresponding 2R, 3S isomers (3, 15b, and 18b).

  DOI：

  10.1021/jo971824a