Acetic acid (2S,3R,4S,5R,6R)-3,5-diacetoxy-2-{(S)-2-acetoxy-2-[5-(acetyl-phenyl-hydrazonomethyl)-2-phenyl-2H-pyrazol-3-yl]-ethoxy}-6-acetoxymethyl-tetrahydro-pyran-4-yl ester | 3082-94-8

• 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: Acetic acid (2S,3R,4S,5R,6R)-3,5-diacetoxy-2-{(S)-2-acetoxy-2-[5-(acetyl-phenyl-hydrazonomethyl)-2-phenyl-2H-pyrazol-3-yl]-ethoxy}-6-acetoxymethyl-tetrahydro-pyran-4-yl ester
• CAS: 3082-94-8
• 化学式: C₃₆H₄₀N₄O₁₃
• 分子量: 736.733
• InChiKey: DWTBEPPOLBZULC-VIGRIJFQSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-3,5-diacetoxy-2-{(S)-2-acetoxy-2-[5-(acetyl-phenyl-hydrazonomethyl)-2-phenyl-2H-pyrazol-3-yl]-ethoxy}-6-acetoxymethyl-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到Acetic acid N'-[1-{5-[(S)-1-hydroxy-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-1-phenyl-1H-pyrazol-3-yl}-meth-(E)-ylidene]-N-phenyl-hydrazide
  参考文献：
  名称：

  Hydrophilically functionalized pyrazoles from sugars11Enantiopure Building Blocks from Sugars. Part 22. For Part 21, see Ref.[1].—Presented, in part, at the 9th European Carbohydrate Symposium, Utrecht, The Netherlands, July 1997; Abstract E1.

  摘要：

  An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-alpha-D-glucopyranosyl-D-fructose (palatinose(R), isomaltulose) into 5-[(1'S)-1',2'-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1S)-2-(alpha-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3-carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00137-2
• 作为产物：
  描述：

  2-(hydroxymethyl)-6-[(5E,6E)-2,3,4-trihydroxy-5,6-bis(phenylhydrazinylidene)hexoxy]oxane-3,4,5-triol 、 乙酸酐 反应 3.0h， 以79%的产率得到Acetic acid (2S,3R,4S,5R,6R)-3,5-diacetoxy-2-{(S)-2-acetoxy-2-[5-(acetyl-phenyl-hydrazonomethyl)-2-phenyl-2H-pyrazol-3-yl]-ethoxy}-6-acetoxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Hydrophilically functionalized pyrazoles from sugars11Enantiopure Building Blocks from Sugars. Part 22. For Part 21, see Ref.[1].—Presented, in part, at the 9th European Carbohydrate Symposium, Utrecht, The Netherlands, July 1997; Abstract E1.

  摘要：

  An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-alpha-D-glucopyranosyl-D-fructose (palatinose(R), isomaltulose) into 5-[(1'S)-1',2'-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1S)-2-(alpha-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3-carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00137-2