Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester | 647021-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4S,5R,6R)-3,4-diacetyloxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-5-[(2,2,2-trichloroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 647021-33-8
• 化学式: C₂₆H₃₆Cl₃NO₁₄
• 分子量: 692.929
• InChiKey: FQFAKJRRVIOECD-PMGLHVRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.17h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620
• 作为产物：
  描述：

  (2R,3S,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 四氧化锇 、 quinuclidine N-oxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 甲基磺酸酐 作用下， 以 甲醇 、 二苯醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 106.33h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620