5,6,7,9,10-penta-O-acetyl-4,8-anhydro-1,3-dideoxy-D-erythro-D-galacto-dec-2-ulose | 848421-15-8

• 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: 5,6,7,9,10-penta-O-acetyl-4,8-anhydro-1,3-dideoxy-D-erythro-D-galacto-dec-2-ulose
• CAS: 848421-15-8
• 化学式: C₂₀H₂₈O₁₂
• 分子量: 460.435
• InChiKey: UBIFMFDNAKPTAU-RFVXBFLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  157.8
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5,6,7,9,10-penta-O-acetyl-4,8-anhydro-1,3-dideoxy-D-erythro-D-galacto-dec-2-ulose 在 ammonia borane 、 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 4,8-anhydro-1,3-dideoxy-D-ribo-L-manno-decitol
  参考文献：
  名称：

  Synthesis of C-glycosides related to glycero-β-d-manno-heptoses

  摘要：

  Reducing heptopyranoses of the D-glycero-D-manno- and L-glycero-D-manno-configuration were converted in good overall yields into beta-anomeric C-glycosides via condensation with pentane-2,4-dione, followed by sodium methoxide-induced enrichment of the beta-anomeric products and subsequent O-acetylation. The resulting 2-oxo-propyl glycosides were further transformed into separable similar to1:1 diastereomeric mixtures of (S)- and (R)-2-hydroxy derivatives. The configuration of the additional stereogenic centre was assigned on the basis of NMR data obtained from the corresponding Dale-Mosher esters. Finally, phosphorylation of the D-glycero-D-manno-heptose analogues using the phosphoramidite procedure and deprotection furnished the (S)- and (R)-2-phosphate derivatives in good yields. The compounds serve as substrate analogues for enzymes involved in bacterial ADP heptose biosynthesis and glycosyl transfer reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.065
• 作为产物：
  描述：

  1-[(3S,4R,5S,6R)-6-((R)-1,2-Dihydroxy-ethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yl]-propan-2-one 、 乙酸酐 在 sodium methylate 、 吡啶 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以161 mg的产率得到5,6,7,9,10-penta-O-acetyl-4,8-anhydro-1,3-dideoxy-D-erythro-D-galacto-dec-2-ulose
  参考文献：
  名称：

  Synthesis of C-glycosides related to glycero-β-d-manno-heptoses

  摘要：

  Reducing heptopyranoses of the D-glycero-D-manno- and L-glycero-D-manno-configuration were converted in good overall yields into beta-anomeric C-glycosides via condensation with pentane-2,4-dione, followed by sodium methoxide-induced enrichment of the beta-anomeric products and subsequent O-acetylation. The resulting 2-oxo-propyl glycosides were further transformed into separable similar to1:1 diastereomeric mixtures of (S)- and (R)-2-hydroxy derivatives. The configuration of the additional stereogenic centre was assigned on the basis of NMR data obtained from the corresponding Dale-Mosher esters. Finally, phosphorylation of the D-glycero-D-manno-heptose analogues using the phosphoramidite procedure and deprotection furnished the (S)- and (R)-2-phosphate derivatives in good yields. The compounds serve as substrate analogues for enzymes involved in bacterial ADP heptose biosynthesis and glycosyl transfer reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.065