3-acetamido-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol | 271243-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamido-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol
• 英文别名: N-[(2R,3R,4R,5R,6R)-2-[[dimethoxy(oxido)phosphaniumyl]methyl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 271243-87-9
• 化学式: C₁₁H₂₂NO₈P
• 分子量: 327.271
• InChiKey: ODJSCEZVQBFWAR-ORMBPQIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-acetamido-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol 在 吡啶 作用下， 以95%的产率得到3-acetamido-4,5,7-tri-O-acetyl-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route

  摘要：

  Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH2P(O)(OMe)(2) to glyconolactones followed by Et3SiH-TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four beta-linked pyranose derivatives (D-galacto, 2-azido-2-deoxy-D-galacto, D-gluco, D-manno) and one beta-linked furanose derivative (D-manno). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et3SiH-BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00477-2
• 作为产物：
  描述：

  3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以98%的产率得到3-acetamido-2,6-anhydro-1,3-dideoxy-1-dimethoxyphosphoryl-D-glycero-L-manno-heptitol
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route

  摘要：

  Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH2P(O)(OMe)(2) to glyconolactones followed by Et3SiH-TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four beta-linked pyranose derivatives (D-galacto, 2-azido-2-deoxy-D-galacto, D-gluco, D-manno) and one beta-linked furanose derivative (D-manno). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et3SiH-BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00477-2

文献信息

• Stereoselective synthesis of C-glycosylphosphonates from their ketols. Reconsideration of an abandoned route
  作者：Alessandro Dondoni、Alberto Marra、Claudia Pasti

  DOI：10.1016/s0957-4166(99)00477-2

  日期：2000.1

  Isosteric phosphonate analogues of glycosyl 1-phosphates have been obtained by addition of LiCH2P(O)(OMe)(2) to glyconolactones followed by Et3SiH-TMSOTf reductive dehydroxylation of the resultant ketols. The compounds prepared include four beta-linked pyranose derivatives (D-galacto, 2-azido-2-deoxy-D-galacto, D-gluco, D-manno) and one beta-linked furanose derivative (D-manno). In the latter case the ketol was activated as its 2-acetate. In agreement with an observation in another laboratory, the dehydroxylation of a model ketol phosphonate failed with the use of Et3SiH-BF3. Et2O. (C) 2000 Elsevier Science Ltd. All rights reserved.