(3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one | 493034-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one
• CAS: 493034-00-7
• 化学式: C₂₅H₃₈O₅Si
• 分子量: 446.659
• InChiKey: OENYARNUHLPPMZ-KSPOJXDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one 在 silver perchlorate 、 三乙胺 、 tin(ll) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.25h， 生成 (2R,3S,4R,7S,8R,9R,10R,11S)-2,8-bis-[(tert-butyldimethyl)silyloxy]-3,7,9-trimethyl-4-O-[2'-deoxy-2'-iodo-3',4'-bis-O-(tert-butyldimethyl)silyl-6'-bromo-β-D-glucopyranosyl]-10-[(benzoyl)oxy]-11-methoxy-13-trimethylsilyl-tridec-4-ol-12-yn-6-one
  参考文献：
  名称：

  2-Deoxy-2-iodo-β-glucopyranosyl Fluorides:  Mild and Highly Stereoselective Glycosyl Donors for the Synthesis of 2-Deoxy-β-glycosides from β-Hydroxy Ketones

  摘要：

  2-Deoxy-2-iodo-beta-glucopyranosyl fluoride 14 is a highly stereoselective glucopyranosyl donor that may be activated under mild conditions. Application of this new glycosyl donor to the glycosidation reactions of a variety of acceptors including beta-hydroxy ketones affords beta-glycosides with high efficiency and stereoselectivity.

  DOI：

  10.1021/ol027257h
• 作为产物：
  描述：

  Benzoic acid (1R,2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-1-((S)-1-methoxy-prop-2-ynyl)-2,4-dimethyl-5-triethylsilanyloxy-hexyl ester 在 三氟乙酸 、 吡啶 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 水 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.33h， 以94%的产率得到(3S,4R,5R,6R,7S)-3,5-dimethyl-4-[(tert-butyldimethyl)silyloxy]-6-[(benzoyl)oxy]-7-methoxy-non-8-yn-2-one
  参考文献：
  名称：

  2-Deoxy-2-iodo-β-glucopyranosyl Fluorides:  Mild and Highly Stereoselective Glycosyl Donors for the Synthesis of 2-Deoxy-β-glycosides from β-Hydroxy Ketones

  摘要：

  2-Deoxy-2-iodo-beta-glucopyranosyl fluoride 14 is a highly stereoselective glucopyranosyl donor that may be activated under mild conditions. Application of this new glycosyl donor to the glycosidation reactions of a variety of acceptors including beta-hydroxy ketones affords beta-glycosides with high efficiency and stereoselectivity.

  DOI：

  10.1021/ol027257h